基于环氧化合物以及共轭烯炔的环化反应研究
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摘要
环状(杂环或者碳环)化合物广泛存在于大多数具有重要生物活性的天然产物和药物分子中。因此,发展一些新型有效的环化/环加成反应对于天然产物全合成和发现有潜在生物活性的分子有着十分重要的意义。本论文的研究工作有两大部分组成：(1)环氧乙烷衍生物的环化反应及机理研究；(2)缺电子烯炔化合物的环化反应研究。
在论文的第一部分我们首次实现了活化的环氧化合物在路易斯酸催化下的碳-碳键选择性断裂并形成羰基叶立德中间体,该中间体能被醛所捕获。首先,我们设计合成了一系列环氧乙烷基二酮类化合物。经过条件优化,我们发现该化合物和醛在Yb(OTf)3的催化下,能以高非对映选择性和高化学选择性得到多取代的1,3-二氧杂环戊烷类化合物。当我们把环氧乙烷的活化基团换成二酯时,实现了该类化合物和醛的化学选择性环化。经过大量的条件摸索,最终在Sn(OTf)2做催化剂时,得到了基于C-O键断裂的环化产物；在Ni(ClO4)2做催化剂时,得到了基于C-C键断裂的环化产物,提出了导致这种不同断键的可能反应机制,并对该机制给予计算化学和实验上的验证。最后我们还实现了Ni(ClO4)2催化下1-芳基环氧乙烷和环氧乙烷基二酯的环加成反应,值得说明的是,在该反应中Ni(ClO4)2起到了双活化的功能。
在论文的第二部分我们以三乙胺为碱,实现了缺电子烯炔和巴豆酸酯衍生的锍盐的环化反应,可以快速高效地得到一系列多官能团化的4-亚烷基二环[3.1.0]己烯类衍生物。我们还发展了缺电子烯酮和修饰的MBH产物在三苯基膦催化下的[4+1]环加成反应,以高区域选择性和高非对映选择性构建了一系列多取代的二氢呋喃产物。在该反应中修饰的MBH产物是作为一碳组分参与到反应中的,不同于Lu等人报道的修饰的MBH产物作为三碳组分参与的[3+n]环加成反应。
Cyclic compounds are present in many natural products and medicinal molecules with biological activity. Therefor, it is very important to develop some novel and efficient cyclization reactions for synthesis of natural products and construction of a wide range of molecules with potential biological activity. This thesis mainly consist of two parts:(1) cyclization of oxirane derivatives and their mechanism study,(2) cyclization of electron-deficient enynes.
In the first part, we established for the first time an efficient approach to carbonyl ylides which trapped with aldehydes by Lewis acid catalyzed chemoselective C-C bond hetorolysis of activated oxiranes. Initially, We synthesized various rationally designed aryl oxiranyl diketones. After numerous attempts, we found that the reaction of aryl oxiranyl diketones and aldehydes proceeded smoothly to afford highly substituted1,3-dioxolanes with excellent diasteroselectivity and chemoselectivity under the catalysis of Yb(OTf)3. When the activated groups were switched to dicarboxylates, we achieved chemodivergent cycloaddtion reactions of activated oxiranes with aldehydes. The reaction worked well to produce the corresponding cycloadduts with C-O bond cleavage of oxiranes under the catalysis of Sn(OTf)2, however, the expected1,3-dioxolanes with C-C bond cleavage of oxiranes were obtained when the Ni(ClO4)2was involved. Based on a series of control experiments and computational study, a mechanism was proposed. Finally, the cycloaddition reactions of styrenyl epoxides and aryl oxiranyl dicarboxylates catalyzed by Ni(ClO4)2was also achieved in mild conditions. It is noteworthy that dual activation of both the two reagents is the key to this reaction.
In the last part, we developed a novel tandem Michael addition and ylide annulation of a crotonate-derived sulfur ylide with readily available electron-deficient enynes catalyzed by Et3N, which provide a rapid, efficient and selective route to multi-functionalized4-alkylidenebicyclo-[3.1.0]hex-2-enes. We also discovered an unexpected phosphine-catalyzed regio-and diastereoselective [4+1] annulation reaction of modified Morita-Baylis-Hillman adducts with activated enones to afford multifunctionalized dihydrofurans. In these annulations, Morita-Baylis-Hillman carbonates act as the one carbon unit, which is distinguished from Lu et al. reported modified allylic compounds as the three carbon units in [3+n] annulation reactions.
在论文的第一部分我们首次实现了活化的环氧化合物在路易斯酸催化下的碳-碳键选择性断裂并形成羰基叶立德中间体,该中间体能被醛所捕获。首先,我们设计合成了一系列环氧乙烷基二酮类化合物。经过条件优化,我们发现该化合物和醛在Yb(OTf)3的催化下,能以高非对映选择性和高化学选择性得到多取代的1,3-二氧杂环戊烷类化合物。当我们把环氧乙烷的活化基团换成二酯时,实现了该类化合物和醛的化学选择性环化。经过大量的条件摸索,最终在Sn(OTf)2做催化剂时,得到了基于C-O键断裂的环化产物；在Ni(ClO4)2做催化剂时,得到了基于C-C键断裂的环化产物,提出了导致这种不同断键的可能反应机制,并对该机制给予计算化学和实验上的验证。最后我们还实现了Ni(ClO4)2催化下1-芳基环氧乙烷和环氧乙烷基二酯的环加成反应,值得说明的是,在该反应中Ni(ClO4)2起到了双活化的功能。
在论文的第二部分我们以三乙胺为碱,实现了缺电子烯炔和巴豆酸酯衍生的锍盐的环化反应,可以快速高效地得到一系列多官能团化的4-亚烷基二环[3.1.0]己烯类衍生物。我们还发展了缺电子烯酮和修饰的MBH产物在三苯基膦催化下的[4+1]环加成反应,以高区域选择性和高非对映选择性构建了一系列多取代的二氢呋喃产物。在该反应中修饰的MBH产物是作为一碳组分参与到反应中的,不同于Lu等人报道的修饰的MBH产物作为三碳组分参与的[3+n]环加成反应。
Cyclic compounds are present in many natural products and medicinal molecules with biological activity. Therefor, it is very important to develop some novel and efficient cyclization reactions for synthesis of natural products and construction of a wide range of molecules with potential biological activity. This thesis mainly consist of two parts:(1) cyclization of oxirane derivatives and their mechanism study,(2) cyclization of electron-deficient enynes.
In the first part, we established for the first time an efficient approach to carbonyl ylides which trapped with aldehydes by Lewis acid catalyzed chemoselective C-C bond hetorolysis of activated oxiranes. Initially, We synthesized various rationally designed aryl oxiranyl diketones. After numerous attempts, we found that the reaction of aryl oxiranyl diketones and aldehydes proceeded smoothly to afford highly substituted1,3-dioxolanes with excellent diasteroselectivity and chemoselectivity under the catalysis of Yb(OTf)3. When the activated groups were switched to dicarboxylates, we achieved chemodivergent cycloaddtion reactions of activated oxiranes with aldehydes. The reaction worked well to produce the corresponding cycloadduts with C-O bond cleavage of oxiranes under the catalysis of Sn(OTf)2, however, the expected1,3-dioxolanes with C-C bond cleavage of oxiranes were obtained when the Ni(ClO4)2was involved. Based on a series of control experiments and computational study, a mechanism was proposed. Finally, the cycloaddition reactions of styrenyl epoxides and aryl oxiranyl dicarboxylates catalyzed by Ni(ClO4)2was also achieved in mild conditions. It is noteworthy that dual activation of both the two reagents is the key to this reaction.
In the last part, we developed a novel tandem Michael addition and ylide annulation of a crotonate-derived sulfur ylide with readily available electron-deficient enynes catalyzed by Et3N, which provide a rapid, efficient and selective route to multi-functionalized4-alkylidenebicyclo-[3.1.0]hex-2-enes. We also discovered an unexpected phosphine-catalyzed regio-and diastereoselective [4+1] annulation reaction of modified Morita-Baylis-Hillman adducts with activated enones to afford multifunctionalized dihydrofurans. In these annulations, Morita-Baylis-Hillman carbonates act as the one carbon unit, which is distinguished from Lu et al. reported modified allylic compounds as the three carbon units in [3+n] annulation reactions.
引文
[1]a) A. Padwa, in 1,3-Dipolar Cycloaddition Chemistry, Vol.1, Wiley, New York, 1984; b) A. Padwa, in 1,3-Dipolar Cycloaddition Chemistry, Vol.2, Wiley, New York,1984; c) R. Huisgen, in Advances in Cycloaddition, Vol.1 (Ed:D. P. Curran), JAI Press Inc., Greenwich,1988, pp.1-32; d) P. Deshong, S. W. Lander, Jr. J. M. Leginus, C. M. Dicken, in Advances in Cycloaddition, Vol.1 (Ed:D. P. Curran), JAI Press Inc., Greenwich,1988, pp.87-128; e) K. V. Gothelf, K. A. J(?)rgensen. Chem. Rev.1998,98,863; f) S. Kanemasa, Synlett 2002,1371; g) A. Padwa, W. H. Pearson, in The Chemistry of Heterocyclic Compounds:Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, Vol.59, Wiley and Sons, New York, 2002; h) H. Pellissier, Tetrahedron 2007,63,3235; i) V. Nair, T. D. Suja, Tetrahedron 2007,63,12247; j) L. M. Stanley, M. P. Sibi, Chem. Rev.2008,108, 2887; k) A. Hassner, in Topics in Heterocyclic Chemistry:Synthesis of Heterocycles via Cycloadditions I, Vol.12, Springer-Verlag Berlin Heidelberg, 2008; 1) M. Kissane, A. R. Maguire, Chem. Soc. Rev.2010,39,845; m) S. Kanemasa, Heterocycles 2010,82,87.
[2]R. Hoffmann, R. B. Woodward, J. Am. Chem. Soc.,1965,87,2046.
[3]L.1. Smith, Chem. Rev.1938,23,193.
[4]a) R. Huisgen, Angew. Chem.1963,75,604; b) R. Huisgen, G. Szeimies, L Mobius, Chem. Ber.1967,100,2494; c) R. Huisgen, Angew. Chem., Int. Ed. Engl. 1963,2,565; d) R. Huisgen, J. Org. Chem.1968,31,2291; e) R. Huisgen, J. Org. Chem.1976,41,403; f) R. Huisgen, The Adventure Playground of Mechanisms and Novel Reactions:Profiles, Pathways and Dreams; (Ed.; J. I. Seeman,) American Chemical Society:Washington, DC.1994.
[5]a) R. Sustmann, Tetrahedron Lett.1971,12,2717; b) R. Sustmann, Pure Appl. Chem.1974,40,569.
[6]T. Curtius, Ber. Dtsch. Chem. Ges.1883,16,2230.
[7]E. Buchner, T. Curtius, Ber. Dtsch. Chem. Ges.1885,18,2371.
[8]a) W. Dieckman, Ber. Dtsch. Chem. Ges.1890,23,1024; b) W. Dieckman, Ber. Dtsch. Chem. Ges.1910,43,1024.
[9]K. N. Houk, J. Gonzalez, Y. Li, Acc. Chem. Res.1995,28,81 and references cited therein.
[10]a) R. Huisgen, In 1,3-Dipolar Cycloaddition Chemistry; (Ed:A. Padwa) Wiley: New York,1984; Vol.1, p 1; b) A. Padwa, In Comprehensive Organic Synthesis; (Eds:B. M. Trost, I. Flemming,) Pergamon Press:Oxford,1991; Vol.4, p 1069.
[11]a) E. F. Ullman, J. E. Milks, J. Am. Chem. Soc.1962,84,1315; b) E. F. Ullman, J. E. Milks, J. Am. Chem. Soc.1964,86,3814; c)E. F. Ullman, W A. Henderson jr., J. Am. Chem. Soc.1966,88,4942.
[12]W. J. Linn, R. E. Benson, J. Am. Chem. Soc.1965,87,3657.
[13]a) P. C. Petrellis, H. Dietrich, E. Meyer, G. W. Griffin, J. Am. Chem. Soc.1967, 89,1967; b) G. W. Griffin, Angew. Chem. Int. Ed. Engl.1971,10,537; c) I. J. Lev, K. lshikawa, N. S. Bhacca, G. W. Grifin, J. Org. Chem.1976,41,2654; d) J. P. K. Wong, A. A. Fahmi, G.W. Griffin, N. S. Bhacca, Tetrahedron 1981,37, 3345.
[14]G. A. Lee, J. Org. Chem.41,1976,41,2656.
[15]R. Huisgen, Angew. Chem. Int. Ed. Engl.1977,16,572 and references cited therein.
[16]P. Clawson, D. A. Whiting, J. Chem. Soc. Perkin Trans 1,1990,1193, and references cited therein.
[17]a) H. S. Gill, J. A. Landgrebe, Tetrahedron Lett.1982,23,5099; b) H. S. Gill, J. A. Landgrebe, J. Org. Chem.1983,48,1051.
[18]N. Shimizu, P. D. Bartlett, J. Am. Chem. Soc.1978,100,4260.
[19]a) M. Bekhazi, J. Warkentin, J. Am. Chem. Soc.1983,105,1289; c) M. Bekhazi, P. A. Risbood, J. Warkentin, J. Am. Chem. Soc.1983,105,5675; d) P. Couture, J. K. Terlouw, J. Warkentin, J. Am. Chem. Soc.1996,118,4214; e) J. Warkentin, J. Chem. Soc., Perkin Trans.1,2000,2161.
[20]M. Hojo, M. Ohkuma, N. Ishibashi, A. Hosomi, Tetrahedron Lett.1993,34, 5943.
[21]a) M. Hojo, H. Aihara, H. Ito, A. Hosomi, Tetrahedron Lett.1996,37,9241; b) M. Hojo, H. Aihara, Y. Suginohara, K. Sakata, S.-Y. Nakamura, C. Murakami, A. Hosomi, J. Org. Chem.1997,62,8610.
[22]M. Hojo, H. Aihara, A. Hosomi, J. Am. Chem. Soc.1996,118,3533.
[23]a) P. De March, R. Huisgen, J. Am. Chem. Soc.1982,104,4952; b) R. Huisgen, P. De March, J. Am. Chem. Soc.1982,104,4953.
[24]a) A. Padwa, S. P. Carter, H. Nimmesgern, J. Org. Chem.1986,51,1157; b) A. Padwa, P. D. Stull, Tetrahedron Lett 1987,28,5470; c) A. Padwa, S. P. Carter, H. Nimmesgern, P. D. Stull, J. Am. Chem.1988,110,2894; d) A. Padwa, G. E. Fryxell, L. Zhi, J. Org. Chem.1988,53,2857; e) A. Padwa, R. L. Chinn, S. F. Hornbukle, L. Zhi, Tetrahedron Lett 1989,30,301; f) A. Padwa, G. E. Fryxell, L. Zhi, J. Am. Chem.1990,112,3100; g) A. Padwa, R. L. Chinn, S. F. Hornbukle, L. Zbi, J. Org. Chem.1991,56,3271; h) A. Padwa, S. F. Hornbukle, Chem. Rev. 1991,91,263; i) A. Padwa, V. P. Sandanayaka, E. A. Certis, J. Am. Chem.1994, 116,2667; j) E. A. Certis, V. P. Sandanayaka, A. Padwa, Tetrahedron Lett 1995, 36,1989;k) A. Padwa, M. D. Weingarten, Chem. Rev.1996,96,223; 1) A. Padwa, Top. Curr. Chem.1997,189,121; m) A. Padwa, Helv. Chim. Acta.2005,88, 1357; n) G. Mehta, S. Muthusamy, Tetrahedron 2002,58,9477; o) M. P. Doyle, D. C. Forbes, M. N. Protopopova, S. A. Stanley, M. M. Vasbinder, K. R. Xavier. J. Org. Chem.1997,62,7210; p) A. E. Russell, J. Brekan, L. Gronenberg, M. P. Doyle, J. Org. Chem.2004,69,5269; q) H. Suga, Y. Ebiura, K. Fukushima, A. Kakehi, T. Baba, J. Org. Chem.2005,70,10782.
[25]a) D. M. Hodgson, P. A. Stupple, C. Johnstone, Tetrahedron Lett.1997,38,6471; b) D. M. Hodgson, A. H. Labande, F. Y. M. Pierard, M. A. E. Castro, J. Org. Chem.2003,68,6153; c) D. M. Hodgson, R. Glen, A. J. Redgrave, Tetrahedron Lett.2002,43,3927;d) D. M. Hodgson, R. Glen, G. H. Grant, A. J. Redgrave, J. Org. Chem.2003,68,581; e) M. P. Doyle, D. C. Forbes, Chem. Rev.1998,98, 911; f) H. Suga, H. Ishida, T. Ibaba, Tetrahedron Lett.1998,39,3165; g) S. Kitagaki, M. Anada, O. Kataoka, K. Matsuno, C. Umeda, N. Watanabe, S. Hashimoto,J. Am. Chem.1999,121,1417; h) S. Kitagaki, M. Yasugahira, M. Anada, M. Yakajima, S. Hashimoto, Tetrahedron Lett.2000,41,5931; i) D. M. Hodgson, F. Y. T. M. Pierard, P, A. Stupple, Chem. Soc. Rev.2001,30,50.
[26]V. V. Nikolaev, A. Linden, H. Heimgarner, Helv. Chim. Acta.2007,90,2330.
[27]For reviews on Lewis acid catalyzed reactions, please see:a) Selectivities in Lewis Acid Promoted Reactions (Eds:D. Schinzer), Kluwer, Dordrecht,1989; b) R. W. Marshman, Aldrichimica Acta,1995,28,77; c) M. Santelli, J. M. Pons, in Lewis Acids and Selectivity in Organic Synthesis, (Eds:M. Santelli, J. M. Pons), CRC Press, Boca Raton,1996; d) H. Yamamoto, in Lewis Acid Reagents:A. Practical Approach, (Ed:H. Yamamoto), Oxford University Press. Oxford,1999; e) S. Kobayashi, Eur. J. Org. Chem.1999,15; f) H. Yamamoto, in Lewis Acids in Organic Synthesis, vol.1-2 (Ed:H. Yamamoto), Willey-VCH, Weinheim,2000; g) S. Kobayashi, M. Sugiura, H. Kitagawa, W. W. L. Lam, Chem. Rev.2002,102, 2227; h) C-Y Wang, Z-F Xi, Chem. Soc. Rev.2007,36,1395; i) G. Bartoli, M. Locatelli, P. Melchiorre, L. Sambri, Eur. J. Org. Chem.2007,2037; j) R. Dalpozzo, G. Bartoli, L. Sambri, P. Melchiorre, Chem. Rev.2010,110,3501; k) S. Antoniotti, V. Dalla, E. Dunach, Angew. Chem., Int. Ed.2010,49,7860; 1) S. Kobayashi, Y. Yamashita, Ace. Chem. Res.2011,44,5%.
[28]R. F. Sweis, M. P. Schramm, S. A. Kozmin, J. Am. Chem.2004,126,7442.
[29]H. Li, R. P. Hsung, K. A. DeKorver, Y. Wei, Org. Lett.2010,12,3780.
[30]J. M. O'Brien, J. S. Kingsbury, J. Org. Chem.2011,76,1662.
[31]a) H.-U. Reissig, R. Zimmer, Chem. Rev.2003,103,1151; b) M. Yu, B. L. Pagenkopf, Tetrahedron 2005,61,321; c) Y. Xiao, J. Zhang, in Handbook of Cyclization Reactions, (Ed:S. Ma), Willey-VCH:Weinheim,2010, Vol.2, p733.
[32]M. Shi, B. Xu, Tetrahedron Lett.2003,44,3839.
[33]a) P. D. Pohlhaus, J. S. Johnson, J. Org. Chem.2005,70,1057; b) P. D. Pohlhaus, J. S. Johnson, J. Am. Chem. Soc.2005,127,16014; c) P. D. Pohlhaus, S. D. Sanders, A. T. Parsons, W. Li, J. S. Johnson, J. Am. Chem. Soc.2008,130,8642; d) A. T. Parsons, J. S. Johnson, J. Am. Chem. Soc.2009,131,3122; e) A. T. Parsons, A. G. Smith, A. J. Neel, J. S. Johnson, J. Am. Chem. Soc.2010,132, 9688.
[34]For reviews, see:a) J. P. A. Harrity, O. Provoost, Org. Biomol. Chem.2005,3, 1349; b) R. P. Hsung, A. V. Kurdyumov, N. Sydorenko, Eur. J. Org. Chem.2005, 23.
[35]Y. R. Lee, D. H. Kim, J.-J. Shim, S. K. Kim, J. H. Park, J. S. Cha, C.-S. Lee, Bull. Korean Chem. Soc.2002,23,998.
[36]A. V. Kurdyumov, N. Lin, R.d P. Hsung, G. C. Gullickson, K. P. Cole, N. Sydorenko, J. J. Swidorski, Org. Lett.2006,8,191.
[37]G. Bartoli, K. Babiuch, M. Bosco, A. Carlone, P. Galzerano, P. Melchiorre, L. Sambri, Synlett 2007,2897.
[38]M. Harmata, Chem. Commun.2010,46,8904 and references cited therein.
[39]O. A. Ivanova, E. M. Budynina, Y. K. Grishin, I. V. Trushkov, P. V. Verteletskii, Angew. Chem., Int. Ed.,2008,47,1107.
[40]H. Gao, X. Wu, J. Zhang, Chem. Commun.2010,46,8764.
[41]Reviews: a) E. Lee-Ruff, G. Mladenova, Chem. Rev. 2003, 103, 1449; b) J. C. Namyslo, D. E. Kaufmann, Chem. Rev. 2003, 103, 1485; c) D. Bellus, B. Ernst, Angew. Chem., Int. Ed. Engl. 1988, 27, 797; d) J. M. Conia, M. Robson, J. Angew. Chem., Int. Ed. Engl. 1975,14, 473.
[42]a) J. Matsuo, S. Sasaki, H. Tanaka, H. Ishibashi, J. Am. Chem. Soc. 2008, 130, 11600; b) J. Matsuo, S. Sasaki, T. Hoshikawa, H. Ishibashi, Org. Lett. 2009, 11, 3822; c) J.Matsuo, R. Okado, H. Ishibashi, Org. Lett. 2010,12, 3266; d) J.Matsuo, S. Sasaki, T. Hoshikawa, H. Ishibashi, Chem. Commun. 2010, 46, 934.
[43]A. T. Parsons, J. S. Johnson, J. Am. Chem. Soc. 2009,131, 14202.
[44]a) M. M. A. R. Moustafa , B. L. Pagenkopf, Org. Lett. 2010, 12, 4732; b) M. M. A. R. Moustafa , A. C. Stevens, B. P. Machin, B. L. Pagenkopf, Org. Lett. 2010, 12, 4736.
[45]E. A. Allart, S. D. R. Christie, G. J. Pritchard, M. R. J. Elsegood, Chem. Commun. 2009, 45, 7339.
[46]a) K. L. Habermas, S. E. Denmark, T. K. Jones, Org. React. (N.Y.) 1994, 45, 1; b) A. Frontier. C. Collison, Tetrahedron 2005, 61, 1511; c) H. Pellissier, Tetrahedron 2005, 61, 6479; d) M. Tius, Eur. J. Org. Chem. 2005, 11, 2193.
[47]W. He, X. Sun, A. J. Frontier, J. Am. Chem. Soc. 2003,125, 14278.
[48]W. He, I. R. Herrick, T. A. Atesin, P. A. Caruana, C. A. Kellenberger. A. J. Frontier,J. Am. Chem. Soc. 2008,130, 1003.
[49]L. Liu, L. Wei, Y.Lu, J. Zhang, Chem. Eur. J. 2010, 16, 11813.
[50]Q. Gao, B. Zheng, J. Li, D. Yang, Org. Lett. 2005, 7, 2185.
[51]H. Tsuji, K.Yamagata, Y. Itoh, K. Endo, M. Nakamura, E. Nakamura, Angew. Chem.Int. Ed. 2007, 46, 8060.
[52]Y. Zhao, B. Li, L. S. Tan, Z. Shen, T. Loh, J. Am. Chem. Soc. 2010, 132, 10242.
[53]a) R. G. Pearson, J. Am. Chem. Soc. 1963, 55, 3533; b) T. Ho, Chem. Rev. 1975, 75, 1; c) T. Ho, in Hard and Soft Acids and Bases Principle in Organic Chemistiy, Academic: New York, 1977; d) T. Ho, Tetrahedron 1985, 41, 3; e) S. Woodward, Tetrahedron 2002, 58, 1017.
[54]N. M. Leonard, L, C. Wieland, R. S. Mohan, Tetrahedron 2002, 58, 8373.
[55]K. Komeyama, K. Takahashi, K. Takaki, Org. Lett. 2008,10, 5119.
[56]K. Komeyama, N. Saigo, M. Miyagi, K. Takaki, Angew. Chem. Int. Ed. 2009, 48, 9875.
[57]J. Godeau, S. Olivero, S. Antoniotti, E. Dufiach, Org. Lett. 2011,13, 3320.
[1]E. Hasegawa, K. Ishiyama, T.Horaguchi, T. Shimizu, J. Org. Chem.1991,56, 1631 and references cited therein.
[2]R. Huisgen, P. De March, J. Am. Chem. Soc.1982,104,4953.
[3]C. Bemaus, J. Font, P. de March, Tetrahedron 1991,47,7713.
[4]G. W. Wang, H. T. Yang, P. Wu, C. B. Miao, Y. Xu, J. Org. Chem.2006,71, 4346.
[5]For Lewis acid catalyzed [3+2] cycloaddition of simple oxiranes with ketones or aldehydes via C-0 bond cleavage, see:a) R. P. Hanzlik, M. Leinwetter, J. Org. Chem.1978,43,438; b) D. Torok, J. Figueroa, W. Scott, J. Org. Chem.1993,58, 7274; c) Z. Zhu, J. Espenson, Organometallics 1997,16,3658:d) R. D. Adams, T. S. Barnard, K. Brosius, J. Organomet. Chem.1999,582,358; e) J. R. Vyvyan, J. A. Meyer, K. D. Meyer, J. Org. Chem.2003,68,9144; f) A. Procopio, R. Dalpozzo, A. De Nino, L. Maiuolo, M. Nardi, B. Russoa,Adv. Synth. Catal.2005, 347,1447; g) P. Krasik, M. Bohemier-Bernard, Q. Yu, Synlett 2005,854; h) J. M. Concellon, J. R. Suarez, S. Garcia-Granda, M. R. Diaz, Org. Lett.2005,7,247; i) F. Benfatti, G. Cardillo, L. Gentilucci, A. Tolomelli, M. Monari, F. Piccinelli, Adv. Synth. Catal.2007,349,1256.
[6]a) Y. Xiao, J. Zhang, Adv. Synth. Catal.2009,351,617; b) Y. Xiao, J. Zhang, Chem. Commun.2009,3594; c) F. Liu, J. Zhang, Angew. Chem. Int. Ed.2009,48, 5505; d) W. Li. Y. Li, J. Zhang, Chem. Eur. J.2010,16,6447.
[7]T. Wang, J. Zhang, Chem. Eur. J.2011,17,86.
[8]a) I. S. Young, M. Kerr, A. Angew. Chem., Int. Ed.2003,42,3023; b) M. P. Sibi, Z. Ma, C. P. Jasperse, J. Am. Chem. Soc.2005,127,5764; c) I. S. Young, M. Kerr, A. J. Am. Chem. Soc.2007,129,1465; d) Y-B. Kang, X-L. Sun, Y. Tang, Angew. Chem., Int. Ed.2007,46,3918.
[9]W. L. F. Armarego, D. D. Perrin, in Purification of Laboratory Chemicals 4th Edition. Butterworth-Heinemann,1999.
[10]V.K. Yadav, K. K. Kapoor, Tetrahedron 1995,51,8573.
[11]M. Ochiai, A. Nakanishi, T. Suefuji, Org. Lett.2000,2,2923.
[12]A. Lattanzi, Adv. Synth. Catal.2006,348,339.
[1]S. Ma, J. Zhang, J. Am. Chem. Soc.2003,125,12386.
[2]S. Chuprakov, V. Gevorgyan, Org. Lett.2007,9,4463.
[3]Selected recent examples of switching the selectivity by Lewis acids, see:a) H. Y. Kim, H.-J. Shih, W. E. Knabe, K. Oh, Angew. Chem. Int. Ed.2009,48,7420; b) H. Y. Kim, K. Oh, Org. Lett.2009,11,5682; c) K. Y. Spangler, C. Wolf, Org. Lett.2009,11,4724; the work from our group:d) L. Liu, J. Zhang, Angew. Chem., Int. Ed.2009,48,6093; e) G. Zhou, J. Zhang, Chem. Commun.2010,46,6593; f) Y. Zhang, F. Liu, J. Zhang, Chem. Eur. J.2010,16,6146; g) G. Lu, T. Yoshino, H. Morimoto, S. Matsunaga, M. Shibasaki, Angew. Chem. Int. Ed.2011,50,4382; h) Z. Wang, Z. Yang, D. Chen, X. Liu, L. Lin, X. Feng, Angew. Chem. Int. Ed. 2011.50,4928.
[4]A. P. Krapcho, J. F. Weimaster, J. Org. Chem.1980,45,4105.
[5]Gaussian 09, Revision B.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, J. E. Peralta, Jr., F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, V. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian, Inc., Wallingford CT, 2010.
[6]The B3LYP functional was used for geometry optimizations, with the standard 6-31+G(d) basis sets for the light elements, and LANL2DZ basis sets containing the pseudo potential for metal atoms. The stabilities of the wavefunctions were tested. The compounds containing Ni prefer triplet ground states so that the unrestricted methods were employed. Frequency calculations were performed to test the obtained stationary points, intermediates (IM) and transition states (TS), and to get their thermochemical corrections. The solvent effects from dichloromethane (ε=8.9) were considered by using polarized continuum model (PCM) at the optimized gas phase structures. The molecular cavities were built up using UFF model. The Gibbs free energies in the solution were obtained by employing the following scheme:ΔGsol=ΔGgas+(ΔEsol-ΔEgas).
[7]For some theoretical reports on [3+2] cycloaddition reactions:a) J. Zhang, W. Shen, M. Li, Eur. J. Org. Chem.2007,4855; b) G. Bentabed-Ababsa, A. Derdour, T. Roisnel, J. A. Saez, P. Perez, E. Chamorro, L. R. Domingo, F. Mongin, J. Org. Chem.2009,74,2120; c) W. Benchouk, S. M. Mekelleche, M. Aurell, L. R. Domingo, Tetrahedron 2009,65,4644; d) L. R. Domingo, J. A. Saez, J. Org. Chem.2011,76,373; e) V. V. Diev, R. R. Kostikov, R. Gleiter, A. P. Molchanov, J. Org. Chem.2006,71,4066.
[8]Using Sn(OTf)2, the energy barrier from IM3 to the trans-transition state is 3.9 kcal/mol, compared with 3.2 kcal/mol to the cis-transition state. The ratio of cis-and trans-product is 3.3:1, closed to the experimental result, see:Table 3-1, entry 17.
[9]Using Ni(ClO4)2, the cycloaddition energy barriers for trans- and cis-products are 15.4 and 9.1 kcal/mol, respectively. This result indicates that there may be tiny trans-product in DCM solution, which is consistent with the experiment result, see:Table 3-1, entry 26.
[10]E. Hasegawa, K. Ishiyama, T. Horaguchi, T. Shimizu, J. Org. Chem.1991,56, 1631.
[11]G. Guanti, L. Banfi, E. Narisano, J. Org. Chem.1992,57,1540.
[12]A. E. Russell, J. Brekan, L. Gronenberg, M. P. Doyle, J. Org. Chem.2004,69, 5269.
[13]M. Igarashi, H. Midorikawa, J. Org. Chem.1964,29,2080.
[14]S. Kanemasa, Y. Oderaotoshi, S. Sakaguchi, H. Yamamoto, J. Tanaka, E. Wada, D. P. Curran, J. Am. Chem. Soc.1998,120,3074.
[1]J. Meinwald, S. S. Labana, M. S. Chadha, J. Am. Chem. Soc.1963,85,582.
[2]a) A. S. Rao, S. K. Paknikar, J. G. Kirtane, Tetrahedron 1983,39,2323; b) J. G. Smith, Synthesis 1984,629.
[3]R. Sudha, K. M. Narasimhan, V. G. Saraswathy, S. Sankararaman, J. Org. Chem. 1996,61,1877.
[4]a) S. Kulasegaram, R. J. Kulawiec, J. Org. Chem.1997,62,6547; b) S. Kulasegaram, R. Kulawiec, Tetrahedron 1998,54,1361.
[5]X. Deng, X. Sun, Y. Tang, J. Org. Chem.2005,70,6537.
[6]D. K. Nielsen, A. G. Doyle, Angew. Chem. Int. Ed.2011,50,6056.
[7]R. F. Lambert, R. J. Hinkle, S. E. Ammann, Y. Lian, J. Liu, S. E. Lewis, R. D. Pike, J. Org. Chem.2011,76,9269.
[8]a) K. A. Bhatia, K. J. Eash, N. M. Leonard, M. C. Oswald, R. S. Mohan, Tetrahedron let.2001,42,8129; b) M. W. C. Robinson, K. S. Pillinger, A. E. Graham, Tetrahedron let.2006,47,5919; c) M. W. C. Robinson, K. S. Pillinger, I. Mabbett, D. A. Timms, A. E. Graham, Tetrahedron 2010,66,8377.
[9]E. J. Corey, M. Chaykovsky, J. Am. Chem. Soc.1965,87,1353.
[10]a) S. Pedragosa-Moreau, C. Morisseau, J. Zylber, A. Archelas, J. Baratti, R. Furstoss, J. Org. Chem.1996,61,7402; b) H. Jin, Z. Li, X. Dong, Org. Biomol. Chem.2004,2,408; c) S. A. Kavanagh, A. Piccinini, E. M. Fleming, S. J. Connon, Org. Biomol. Chem.2008,6,1339; and reference 6.
[1]For leading reviews on ylide reactions, please see: a) E. M. McGarrigle, E.L. Myers, O. Ilia, M. A. Shaw, S. L. Riches, V. K. Aggarwal, Chem. Rev. 2007, 107, 5841; b) Y. Tang, S. Ye, X.-L. Sun, Synlett 2005, 2720; c) V. K. Aggarwal, C. L. Winn, Ace. Chew. Res. 2004, 37, 611; d) H. Lebel, J. F. Marcouxv, C. Molinnaro, A. B. Charette, Chem. Rev. 2003, 103, 977; e) L.-X. Dai, X.-L. Hou, Y.-G. Zhou, Pure Appl. Chem. 1999, 71, 369; f) A.-H. Li, L.-X. Dai, V. K. Aggarwal, Chem. Rev. 1997, 97, 2341; g) X.-L. Sun, Y. Tang, Ace. Chem. Res., 2008, 41, 937; h) V. K. Aggarwal, J. Richardson, Chem. Commun. 2003, 2644.
[2]For selected recent references, see: a) M. G. Unthank, N. Hussain, V. K. Aggarwal, Angew. Chem. Int. Ed. 2006, 45, 7066; b) V. K. Aggarwal, E. Grange, Chem. Eur. J. 2006, 12, 568; c) M. G. Unthank, B. Tavassoli, V. K. Aggarwal, Org. Lett. 2008, 10, 1501; d) L.-W. Ye, X.-L. Sun, C. -Y. Li, Y. Tang, J. Org. Chem. 2007, 72, 1335; e) Q.-G. Wang, X.-M. Deng, B.-H. Zhu, L.-W. Ye, X.-L. Sun, C.-Y. Li, C.-Y. Zhu, Q. Shen, Y. Tang, J. Am. Chem. Soc. 2008, 130, 5408; f) Y. Wang, W. Zhang, J. V. Colandrea, L. S. Jimenez, Tetrahedron 1999, 55, 10659; g) K. Kim, L. S. Jimenez, Tetrahedron: Asymmetry 2001, 12, 999, and references therein.
[3]a) J. R. Neff, R. R. Gruetzmacher, J. E. Nordlander, J. Org. Chem. 1974, 39, 3814; b) Y. Tang, Y.-Z. Huang, L.-X. Dai, J. Sun, W. Xia, J. Org. Chem. 1997, 62, 954; c) S. Ye, Z. Huang, C. Xia, Y. Tang, L. Dai, J. Am. Chem. Soc. 2002, 124, 2432; d) X. Deng, P. Cai, S. Ye, X. Sun, W. Liao, K. Li, Y. Tang, Y. Wu, L. Dai, J. Am. Chem. Soc. 2006,128, 9730.
[4]Y. Zhang, Z. Chen, Y. Xiao, J. Zhang, Chem. Eur. J. 2009, 15, 5208.
[5]a) Y. Xiao, J. Zhang, Angew. Chem. Int. Ed. 2008, 47, 1903; b) X. Yu, H. Ren, Y. Xiao, J. Zhang, Chem. Eur. J. 2008, 14, 8481; c) L. Fan, W. Zhao, W. Jiang, J. Zhang, Chem. Eur. J. 2008, 14, 9139.
[6]a) J. A. Monn, M. J. Valli, S. M. Massey, R. A. Wright, C. R. Salhoff, B. G. Johnson, T. Howe, C. A. Alt, G. A. Rhodes, R. J. Robey, K. R. Griffey, J. P. Tizzano, M. J. Kallman, D. R. Helton, D. D. Schoepp, J. Med. Chem. 1997, 40, 528; b) H. O. Bertrand, A. S. Bessis, J. P. Pin, F. C. Acher, J. Med. Chem. 2002, 45,3171; c) G. Yue, L. Yang, C. Yuan, X. Jiang, B. Liu, Org. Lett.2011,13, 5406; d) Y. Lu, X. Peng, Org. Lett.2011,13,2940.
[7]a) V. Mamane, T. Gress, H. Krause, A. Furstner, J. Am. Chem. Soc.2004,126, 8654; b) Y. Harrak, C. Blaszykowski, M. Bernard, K. Cariou, E. Mainetti, V. Mouries, A. Dhimane,L.Fensterbank, M. Malacria, J. Am. Chem. Soc.2004,126, 8656; c) H. Horie, T. Kurahashi, S. Matsubara, Angew. Chem. Int. Ed.2011,50, 8956; for reviews, see:d) V. Michelet, P. Y. Toullec, J. P. GenTt, Angew. Chem. Int. Ed.2008,47,4268; e) C. Aubert, L. Fensterbank, P. Garcia, M. Malacria, A. Simonneau, Chem. Rev.2011,111,1954.
[8]T. Yao, X. Zhang, R. C. Larock, J. Am. Chem. Soc.2004,126,11164.
[9]M. E. Krafft, J. W. Cran, Synlett 2005,1263.
[10]H. Gershon, L. Shanks, D. E. Gawiak, J. Med. Chem.1916,19,1069.
[1]a) J. I. G. Cadogan, Organophosphorus Reagents in Organic Synthesis, Academic Press:New York,1979; b) R. Bohlmann, In Comprehensive Organic Synthesis, Vol.6, (Eds:B. M. Trost, I. Fleming,) Pergamon:London,1991, Chap.1.7,203; c) R. Sustmann, In Comprehensive Organic Synthesis, Vol.6, (Eds:B. M. Trost, I. Fleming,) Pergamon:London,1991, Chap.2.1,301; c) D. J. Gorin, B. D. Sherry, F. D. Toste, Chem. Rev.2008,108,3351.
[2]a) X. Lu, C. Zhang, Z. Xu, Acc. Chem. Res.2001,34,535; b) D. H. Jr. Valentine, J. H. Hillhouse, Synthesis.2003,317; c) J. L. Methot, W. R. Roush, Adv. Synth. Catal.2004,346,1035; d) X. Lu, Y. Du, C. Lu, Pure. Appl. Chem.2005,77, 1985; e) V. Nair, R. S. Menon, A. R. Sreekanth, N. Abhilash, A. T. Biju, Ace. Chem. Res.2006,39,520; f) L. Ye, J. Zhou, Y. Tang, Chem. Soc. Rev.2008,37, 1140; g) C. E. Aroyan, A. Dermenci, S. J. Miller, Tetrahedron 2009,65,4069; h) Y. Wei, M. Shi, Ace. Chem. Res.2010,43,1005; i) A. Marinetti, A. Voituriez, Synlett 2010,174.
[3]a) C. Zhang, X. Lu, J. Org. Chem.1995,60,2906; b) Z. Xu, X. Lu, Tetrahedron Lett.1997,38,3461; c) Z. Xu, X. Lu, J. Org. Chem.1998,63,5031; d) Z. Xu, X. Lu, Tetrahedron Lett.1999,40,549; e) X. Lu, Z. Lu, X. Zhang, Tetrahedron, 2006,62,457.
[4]a) Y. Du, X. Lu, C. Zhang, Angew. Chem., Int. Ed.,2003,42,1035; b) Y. Du, J. Feng, X. Lu, Org. Lett.,2005,7,1987; c) J. Feng, X. Lu, A. Kong, X. Han, Tetrahedron,2007,63,6035; d) S. Zheng, X. Lu, Org. Lett.,2008,10,4481; e) S. Zheng, X. Lu, Org. Lett.,2009,11,3978; f) S. Zheng, X. Lu, Tetrahedron Lett., 2009,50,4532.
[5]a) Y. Xia, Y. Liang, Y. Chen, M. Wang, L. Jiao, F. Huang, S. Liu, Y. Li, Z. Yu, J. Am. Chem. Soc.2007,129,3470; b) Y. Liang, S. Liu, Y. Xia, Y. Li, Z. Yu, Chem. Eur. J.2008,14,4361.
[6]a) X. Zhu, J. Lan, O. Kwon, J. Am. Chem. Soc.2003,125,4716; b) X. Zhu, A. Schaffner, R. C. Li, O. Kwon, Org. Lett.2005,7,2977; c) E. Mercier, B. Fonovic, C. Henry, O. Kwon, T. Dudding, Tetrahedron Lett.2007,48,3617; d) S. Castellano, H. D. G. Fiji, S. S. Kinderman, M. Watanabe, P. de Leon, F. Tamanoi, O. Kwon, J. Am. Chem. Soc.2007,129,5843.
[7]a) J.-C. Wang, S. S. Ng, M. J. Krische, J. Am. Chem. Soc.2003,125,3682; b) J.-C. Wang, M. J. Krische, Angew. Chem., Int. Ed.2003,42,5855.
[8]a) R. P. Wurz, G. C. Fu, J. Am. Chem. Soc.2005,127,12234; b) J. E. Wilson, G. C. Fu, Angew. Chem., Int. Ed.2006,45,1426.
[9]a) L. Ye, X. Sun, Q. Wang, Y. Tang, Angew. Chem., Int. Ed.2007,46,5951; b) L Ye, X. Han, X. Sun, Y. Tang, Tetrahedron 2008,64,1487; c) X. Han, L.Ye, X. Sun, Y. Tang, J. Org. Chem.2009,74,3394.
[10]a) Y. Xiao, J. Zhang, Adv. Synth. Catal.2009,351,617; b) Y. Xiao, J. Zhang, Chem. Commun.2009,3594; c) F. Liu, J. Zhang, Angew. Chem. Int. Ed.2009,48, 5505; d) W. Li. Y. Li, J. Zhang, Chem. Eur. J.2010,16,6447; e) W. Li, Y. Xiao, J. Zhang, Adv. Synth. Catal.2009,351,3083.
[2]R. Hoffmann, R. B. Woodward, J. Am. Chem. Soc.,1965,87,2046.
[3]L.1. Smith, Chem. Rev.1938,23,193.
[4]a) R. Huisgen, Angew. Chem.1963,75,604; b) R. Huisgen, G. Szeimies, L Mobius, Chem. Ber.1967,100,2494; c) R. Huisgen, Angew. Chem., Int. Ed. Engl. 1963,2,565; d) R. Huisgen, J. Org. Chem.1968,31,2291; e) R. Huisgen, J. Org. Chem.1976,41,403; f) R. Huisgen, The Adventure Playground of Mechanisms and Novel Reactions:Profiles, Pathways and Dreams; (Ed.; J. I. Seeman,) American Chemical Society:Washington, DC.1994.
[5]a) R. Sustmann, Tetrahedron Lett.1971,12,2717; b) R. Sustmann, Pure Appl. Chem.1974,40,569.
[6]T. Curtius, Ber. Dtsch. Chem. Ges.1883,16,2230.
[7]E. Buchner, T. Curtius, Ber. Dtsch. Chem. Ges.1885,18,2371.
[8]a) W. Dieckman, Ber. Dtsch. Chem. Ges.1890,23,1024; b) W. Dieckman, Ber. Dtsch. Chem. Ges.1910,43,1024.
[9]K. N. Houk, J. Gonzalez, Y. Li, Acc. Chem. Res.1995,28,81 and references cited therein.
[10]a) R. Huisgen, In 1,3-Dipolar Cycloaddition Chemistry; (Ed:A. Padwa) Wiley: New York,1984; Vol.1, p 1; b) A. Padwa, In Comprehensive Organic Synthesis; (Eds:B. M. Trost, I. Flemming,) Pergamon Press:Oxford,1991; Vol.4, p 1069.
[11]a) E. F. Ullman, J. E. Milks, J. Am. Chem. Soc.1962,84,1315; b) E. F. Ullman, J. E. Milks, J. Am. Chem. Soc.1964,86,3814; c)E. F. Ullman, W A. Henderson jr., J. Am. Chem. Soc.1966,88,4942.
[12]W. J. Linn, R. E. Benson, J. Am. Chem. Soc.1965,87,3657.
[13]a) P. C. Petrellis, H. Dietrich, E. Meyer, G. W. Griffin, J. Am. Chem. Soc.1967, 89,1967; b) G. W. Griffin, Angew. Chem. Int. Ed. Engl.1971,10,537; c) I. J. Lev, K. lshikawa, N. S. Bhacca, G. W. Grifin, J. Org. Chem.1976,41,2654; d) J. P. K. Wong, A. A. Fahmi, G.W. Griffin, N. S. Bhacca, Tetrahedron 1981,37, 3345.
[14]G. A. Lee, J. Org. Chem.41,1976,41,2656.
[15]R. Huisgen, Angew. Chem. Int. Ed. Engl.1977,16,572 and references cited therein.
[16]P. Clawson, D. A. Whiting, J. Chem. Soc. Perkin Trans 1,1990,1193, and references cited therein.
[17]a) H. S. Gill, J. A. Landgrebe, Tetrahedron Lett.1982,23,5099; b) H. S. Gill, J. A. Landgrebe, J. Org. Chem.1983,48,1051.
[18]N. Shimizu, P. D. Bartlett, J. Am. Chem. Soc.1978,100,4260.
[19]a) M. Bekhazi, J. Warkentin, J. Am. Chem. Soc.1983,105,1289; c) M. Bekhazi, P. A. Risbood, J. Warkentin, J. Am. Chem. Soc.1983,105,5675; d) P. Couture, J. K. Terlouw, J. Warkentin, J. Am. Chem. Soc.1996,118,4214; e) J. Warkentin, J. Chem. Soc., Perkin Trans.1,2000,2161.
[20]M. Hojo, M. Ohkuma, N. Ishibashi, A. Hosomi, Tetrahedron Lett.1993,34, 5943.
[21]a) M. Hojo, H. Aihara, H. Ito, A. Hosomi, Tetrahedron Lett.1996,37,9241; b) M. Hojo, H. Aihara, Y. Suginohara, K. Sakata, S.-Y. Nakamura, C. Murakami, A. Hosomi, J. Org. Chem.1997,62,8610.
[22]M. Hojo, H. Aihara, A. Hosomi, J. Am. Chem. Soc.1996,118,3533.
[23]a) P. De March, R. Huisgen, J. Am. Chem. Soc.1982,104,4952; b) R. Huisgen, P. De March, J. Am. Chem. Soc.1982,104,4953.
[24]a) A. Padwa, S. P. Carter, H. Nimmesgern, J. Org. Chem.1986,51,1157; b) A. Padwa, P. D. Stull, Tetrahedron Lett 1987,28,5470; c) A. Padwa, S. P. Carter, H. Nimmesgern, P. D. Stull, J. Am. Chem.1988,110,2894; d) A. Padwa, G. E. Fryxell, L. Zhi, J. Org. Chem.1988,53,2857; e) A. Padwa, R. L. Chinn, S. F. Hornbukle, L. Zhi, Tetrahedron Lett 1989,30,301; f) A. Padwa, G. E. Fryxell, L. Zhi, J. Am. Chem.1990,112,3100; g) A. Padwa, R. L. Chinn, S. F. Hornbukle, L. Zbi, J. Org. Chem.1991,56,3271; h) A. Padwa, S. F. Hornbukle, Chem. Rev. 1991,91,263; i) A. Padwa, V. P. Sandanayaka, E. A. Certis, J. Am. Chem.1994, 116,2667; j) E. A. Certis, V. P. Sandanayaka, A. Padwa, Tetrahedron Lett 1995, 36,1989;k) A. Padwa, M. D. Weingarten, Chem. Rev.1996,96,223; 1) A. Padwa, Top. Curr. Chem.1997,189,121; m) A. Padwa, Helv. Chim. Acta.2005,88, 1357; n) G. Mehta, S. Muthusamy, Tetrahedron 2002,58,9477; o) M. P. Doyle, D. C. Forbes, M. N. Protopopova, S. A. Stanley, M. M. Vasbinder, K. R. Xavier. J. Org. Chem.1997,62,7210; p) A. E. Russell, J. Brekan, L. Gronenberg, M. P. Doyle, J. Org. Chem.2004,69,5269; q) H. Suga, Y. Ebiura, K. Fukushima, A. Kakehi, T. Baba, J. Org. Chem.2005,70,10782.
[25]a) D. M. Hodgson, P. A. Stupple, C. Johnstone, Tetrahedron Lett.1997,38,6471; b) D. M. Hodgson, A. H. Labande, F. Y. M. Pierard, M. A. E. Castro, J. Org. Chem.2003,68,6153; c) D. M. Hodgson, R. Glen, A. J. Redgrave, Tetrahedron Lett.2002,43,3927;d) D. M. Hodgson, R. Glen, G. H. Grant, A. J. Redgrave, J. Org. Chem.2003,68,581; e) M. P. Doyle, D. C. Forbes, Chem. Rev.1998,98, 911; f) H. Suga, H. Ishida, T. Ibaba, Tetrahedron Lett.1998,39,3165; g) S. Kitagaki, M. Anada, O. Kataoka, K. Matsuno, C. Umeda, N. Watanabe, S. Hashimoto,J. Am. Chem.1999,121,1417; h) S. Kitagaki, M. Yasugahira, M. Anada, M. Yakajima, S. Hashimoto, Tetrahedron Lett.2000,41,5931; i) D. M. Hodgson, F. Y. T. M. Pierard, P, A. Stupple, Chem. Soc. Rev.2001,30,50.
[26]V. V. Nikolaev, A. Linden, H. Heimgarner, Helv. Chim. Acta.2007,90,2330.
[27]For reviews on Lewis acid catalyzed reactions, please see:a) Selectivities in Lewis Acid Promoted Reactions (Eds:D. Schinzer), Kluwer, Dordrecht,1989; b) R. W. Marshman, Aldrichimica Acta,1995,28,77; c) M. Santelli, J. M. Pons, in Lewis Acids and Selectivity in Organic Synthesis, (Eds:M. Santelli, J. M. Pons), CRC Press, Boca Raton,1996; d) H. Yamamoto, in Lewis Acid Reagents:A. Practical Approach, (Ed:H. Yamamoto), Oxford University Press. Oxford,1999; e) S. Kobayashi, Eur. J. Org. Chem.1999,15; f) H. Yamamoto, in Lewis Acids in Organic Synthesis, vol.1-2 (Ed:H. Yamamoto), Willey-VCH, Weinheim,2000; g) S. Kobayashi, M. Sugiura, H. Kitagawa, W. W. L. Lam, Chem. Rev.2002,102, 2227; h) C-Y Wang, Z-F Xi, Chem. Soc. Rev.2007,36,1395; i) G. Bartoli, M. Locatelli, P. Melchiorre, L. Sambri, Eur. J. Org. Chem.2007,2037; j) R. Dalpozzo, G. Bartoli, L. Sambri, P. Melchiorre, Chem. Rev.2010,110,3501; k) S. Antoniotti, V. Dalla, E. Dunach, Angew. Chem., Int. Ed.2010,49,7860; 1) S. Kobayashi, Y. Yamashita, Ace. Chem. Res.2011,44,5%.
[28]R. F. Sweis, M. P. Schramm, S. A. Kozmin, J. Am. Chem.2004,126,7442.
[29]H. Li, R. P. Hsung, K. A. DeKorver, Y. Wei, Org. Lett.2010,12,3780.
[30]J. M. O'Brien, J. S. Kingsbury, J. Org. Chem.2011,76,1662.
[31]a) H.-U. Reissig, R. Zimmer, Chem. Rev.2003,103,1151; b) M. Yu, B. L. Pagenkopf, Tetrahedron 2005,61,321; c) Y. Xiao, J. Zhang, in Handbook of Cyclization Reactions, (Ed:S. Ma), Willey-VCH:Weinheim,2010, Vol.2, p733.
[32]M. Shi, B. Xu, Tetrahedron Lett.2003,44,3839.
[33]a) P. D. Pohlhaus, J. S. Johnson, J. Org. Chem.2005,70,1057; b) P. D. Pohlhaus, J. S. Johnson, J. Am. Chem. Soc.2005,127,16014; c) P. D. Pohlhaus, S. D. Sanders, A. T. Parsons, W. Li, J. S. Johnson, J. Am. Chem. Soc.2008,130,8642; d) A. T. Parsons, J. S. Johnson, J. Am. Chem. Soc.2009,131,3122; e) A. T. Parsons, A. G. Smith, A. J. Neel, J. S. Johnson, J. Am. Chem. Soc.2010,132, 9688.
[34]For reviews, see:a) J. P. A. Harrity, O. Provoost, Org. Biomol. Chem.2005,3, 1349; b) R. P. Hsung, A. V. Kurdyumov, N. Sydorenko, Eur. J. Org. Chem.2005, 23.
[35]Y. R. Lee, D. H. Kim, J.-J. Shim, S. K. Kim, J. H. Park, J. S. Cha, C.-S. Lee, Bull. Korean Chem. Soc.2002,23,998.
[36]A. V. Kurdyumov, N. Lin, R.d P. Hsung, G. C. Gullickson, K. P. Cole, N. Sydorenko, J. J. Swidorski, Org. Lett.2006,8,191.
[37]G. Bartoli, K. Babiuch, M. Bosco, A. Carlone, P. Galzerano, P. Melchiorre, L. Sambri, Synlett 2007,2897.
[38]M. Harmata, Chem. Commun.2010,46,8904 and references cited therein.
[39]O. A. Ivanova, E. M. Budynina, Y. K. Grishin, I. V. Trushkov, P. V. Verteletskii, Angew. Chem., Int. Ed.,2008,47,1107.
[40]H. Gao, X. Wu, J. Zhang, Chem. Commun.2010,46,8764.
[41]Reviews: a) E. Lee-Ruff, G. Mladenova, Chem. Rev. 2003, 103, 1449; b) J. C. Namyslo, D. E. Kaufmann, Chem. Rev. 2003, 103, 1485; c) D. Bellus, B. Ernst, Angew. Chem., Int. Ed. Engl. 1988, 27, 797; d) J. M. Conia, M. Robson, J. Angew. Chem., Int. Ed. Engl. 1975,14, 473.
[42]a) J. Matsuo, S. Sasaki, H. Tanaka, H. Ishibashi, J. Am. Chem. Soc. 2008, 130, 11600; b) J. Matsuo, S. Sasaki, T. Hoshikawa, H. Ishibashi, Org. Lett. 2009, 11, 3822; c) J.Matsuo, R. Okado, H. Ishibashi, Org. Lett. 2010,12, 3266; d) J.Matsuo, S. Sasaki, T. Hoshikawa, H. Ishibashi, Chem. Commun. 2010, 46, 934.
[43]A. T. Parsons, J. S. Johnson, J. Am. Chem. Soc. 2009,131, 14202.
[44]a) M. M. A. R. Moustafa , B. L. Pagenkopf, Org. Lett. 2010, 12, 4732; b) M. M. A. R. Moustafa , A. C. Stevens, B. P. Machin, B. L. Pagenkopf, Org. Lett. 2010, 12, 4736.
[45]E. A. Allart, S. D. R. Christie, G. J. Pritchard, M. R. J. Elsegood, Chem. Commun. 2009, 45, 7339.
[46]a) K. L. Habermas, S. E. Denmark, T. K. Jones, Org. React. (N.Y.) 1994, 45, 1; b) A. Frontier. C. Collison, Tetrahedron 2005, 61, 1511; c) H. Pellissier, Tetrahedron 2005, 61, 6479; d) M. Tius, Eur. J. Org. Chem. 2005, 11, 2193.
[47]W. He, X. Sun, A. J. Frontier, J. Am. Chem. Soc. 2003,125, 14278.
[48]W. He, I. R. Herrick, T. A. Atesin, P. A. Caruana, C. A. Kellenberger. A. J. Frontier,J. Am. Chem. Soc. 2008,130, 1003.
[49]L. Liu, L. Wei, Y.Lu, J. Zhang, Chem. Eur. J. 2010, 16, 11813.
[50]Q. Gao, B. Zheng, J. Li, D. Yang, Org. Lett. 2005, 7, 2185.
[51]H. Tsuji, K.Yamagata, Y. Itoh, K. Endo, M. Nakamura, E. Nakamura, Angew. Chem.Int. Ed. 2007, 46, 8060.
[52]Y. Zhao, B. Li, L. S. Tan, Z. Shen, T. Loh, J. Am. Chem. Soc. 2010, 132, 10242.
[53]a) R. G. Pearson, J. Am. Chem. Soc. 1963, 55, 3533; b) T. Ho, Chem. Rev. 1975, 75, 1; c) T. Ho, in Hard and Soft Acids and Bases Principle in Organic Chemistiy, Academic: New York, 1977; d) T. Ho, Tetrahedron 1985, 41, 3; e) S. Woodward, Tetrahedron 2002, 58, 1017.
[54]N. M. Leonard, L, C. Wieland, R. S. Mohan, Tetrahedron 2002, 58, 8373.
[55]K. Komeyama, K. Takahashi, K. Takaki, Org. Lett. 2008,10, 5119.
[56]K. Komeyama, N. Saigo, M. Miyagi, K. Takaki, Angew. Chem. Int. Ed. 2009, 48, 9875.
[57]J. Godeau, S. Olivero, S. Antoniotti, E. Dufiach, Org. Lett. 2011,13, 3320.
[1]E. Hasegawa, K. Ishiyama, T.Horaguchi, T. Shimizu, J. Org. Chem.1991,56, 1631 and references cited therein.
[2]R. Huisgen, P. De March, J. Am. Chem. Soc.1982,104,4953.
[3]C. Bemaus, J. Font, P. de March, Tetrahedron 1991,47,7713.
[4]G. W. Wang, H. T. Yang, P. Wu, C. B. Miao, Y. Xu, J. Org. Chem.2006,71, 4346.
[5]For Lewis acid catalyzed [3+2] cycloaddition of simple oxiranes with ketones or aldehydes via C-0 bond cleavage, see:a) R. P. Hanzlik, M. Leinwetter, J. Org. Chem.1978,43,438; b) D. Torok, J. Figueroa, W. Scott, J. Org. Chem.1993,58, 7274; c) Z. Zhu, J. Espenson, Organometallics 1997,16,3658:d) R. D. Adams, T. S. Barnard, K. Brosius, J. Organomet. Chem.1999,582,358; e) J. R. Vyvyan, J. A. Meyer, K. D. Meyer, J. Org. Chem.2003,68,9144; f) A. Procopio, R. Dalpozzo, A. De Nino, L. Maiuolo, M. Nardi, B. Russoa,Adv. Synth. Catal.2005, 347,1447; g) P. Krasik, M. Bohemier-Bernard, Q. Yu, Synlett 2005,854; h) J. M. Concellon, J. R. Suarez, S. Garcia-Granda, M. R. Diaz, Org. Lett.2005,7,247; i) F. Benfatti, G. Cardillo, L. Gentilucci, A. Tolomelli, M. Monari, F. Piccinelli, Adv. Synth. Catal.2007,349,1256.
[6]a) Y. Xiao, J. Zhang, Adv. Synth. Catal.2009,351,617; b) Y. Xiao, J. Zhang, Chem. Commun.2009,3594; c) F. Liu, J. Zhang, Angew. Chem. Int. Ed.2009,48, 5505; d) W. Li. Y. Li, J. Zhang, Chem. Eur. J.2010,16,6447.
[7]T. Wang, J. Zhang, Chem. Eur. J.2011,17,86.
[8]a) I. S. Young, M. Kerr, A. Angew. Chem., Int. Ed.2003,42,3023; b) M. P. Sibi, Z. Ma, C. P. Jasperse, J. Am. Chem. Soc.2005,127,5764; c) I. S. Young, M. Kerr, A. J. Am. Chem. Soc.2007,129,1465; d) Y-B. Kang, X-L. Sun, Y. Tang, Angew. Chem., Int. Ed.2007,46,3918.
[9]W. L. F. Armarego, D. D. Perrin, in Purification of Laboratory Chemicals 4th Edition. Butterworth-Heinemann,1999.
[10]V.K. Yadav, K. K. Kapoor, Tetrahedron 1995,51,8573.
[11]M. Ochiai, A. Nakanishi, T. Suefuji, Org. Lett.2000,2,2923.
[12]A. Lattanzi, Adv. Synth. Catal.2006,348,339.
[1]S. Ma, J. Zhang, J. Am. Chem. Soc.2003,125,12386.
[2]S. Chuprakov, V. Gevorgyan, Org. Lett.2007,9,4463.
[3]Selected recent examples of switching the selectivity by Lewis acids, see:a) H. Y. Kim, H.-J. Shih, W. E. Knabe, K. Oh, Angew. Chem. Int. Ed.2009,48,7420; b) H. Y. Kim, K. Oh, Org. Lett.2009,11,5682; c) K. Y. Spangler, C. Wolf, Org. Lett.2009,11,4724; the work from our group:d) L. Liu, J. Zhang, Angew. Chem., Int. Ed.2009,48,6093; e) G. Zhou, J. Zhang, Chem. Commun.2010,46,6593; f) Y. Zhang, F. Liu, J. Zhang, Chem. Eur. J.2010,16,6146; g) G. Lu, T. Yoshino, H. Morimoto, S. Matsunaga, M. Shibasaki, Angew. Chem. Int. Ed.2011,50,4382; h) Z. Wang, Z. Yang, D. Chen, X. Liu, L. Lin, X. Feng, Angew. Chem. Int. Ed. 2011.50,4928.
[4]A. P. Krapcho, J. F. Weimaster, J. Org. Chem.1980,45,4105.
[5]Gaussian 09, Revision B.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, J. E. Peralta, Jr., F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, V. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian, Inc., Wallingford CT, 2010.
[6]The B3LYP functional was used for geometry optimizations, with the standard 6-31+G(d) basis sets for the light elements, and LANL2DZ basis sets containing the pseudo potential for metal atoms. The stabilities of the wavefunctions were tested. The compounds containing Ni prefer triplet ground states so that the unrestricted methods were employed. Frequency calculations were performed to test the obtained stationary points, intermediates (IM) and transition states (TS), and to get their thermochemical corrections. The solvent effects from dichloromethane (ε=8.9) were considered by using polarized continuum model (PCM) at the optimized gas phase structures. The molecular cavities were built up using UFF model. The Gibbs free energies in the solution were obtained by employing the following scheme:ΔGsol=ΔGgas+(ΔEsol-ΔEgas).
[7]For some theoretical reports on [3+2] cycloaddition reactions:a) J. Zhang, W. Shen, M. Li, Eur. J. Org. Chem.2007,4855; b) G. Bentabed-Ababsa, A. Derdour, T. Roisnel, J. A. Saez, P. Perez, E. Chamorro, L. R. Domingo, F. Mongin, J. Org. Chem.2009,74,2120; c) W. Benchouk, S. M. Mekelleche, M. Aurell, L. R. Domingo, Tetrahedron 2009,65,4644; d) L. R. Domingo, J. A. Saez, J. Org. Chem.2011,76,373; e) V. V. Diev, R. R. Kostikov, R. Gleiter, A. P. Molchanov, J. Org. Chem.2006,71,4066.
[8]Using Sn(OTf)2, the energy barrier from IM3 to the trans-transition state is 3.9 kcal/mol, compared with 3.2 kcal/mol to the cis-transition state. The ratio of cis-and trans-product is 3.3:1, closed to the experimental result, see:Table 3-1, entry 17.
[9]Using Ni(ClO4)2, the cycloaddition energy barriers for trans- and cis-products are 15.4 and 9.1 kcal/mol, respectively. This result indicates that there may be tiny trans-product in DCM solution, which is consistent with the experiment result, see:Table 3-1, entry 26.
[10]E. Hasegawa, K. Ishiyama, T. Horaguchi, T. Shimizu, J. Org. Chem.1991,56, 1631.
[11]G. Guanti, L. Banfi, E. Narisano, J. Org. Chem.1992,57,1540.
[12]A. E. Russell, J. Brekan, L. Gronenberg, M. P. Doyle, J. Org. Chem.2004,69, 5269.
[13]M. Igarashi, H. Midorikawa, J. Org. Chem.1964,29,2080.
[14]S. Kanemasa, Y. Oderaotoshi, S. Sakaguchi, H. Yamamoto, J. Tanaka, E. Wada, D. P. Curran, J. Am. Chem. Soc.1998,120,3074.
[1]J. Meinwald, S. S. Labana, M. S. Chadha, J. Am. Chem. Soc.1963,85,582.
[2]a) A. S. Rao, S. K. Paknikar, J. G. Kirtane, Tetrahedron 1983,39,2323; b) J. G. Smith, Synthesis 1984,629.
[3]R. Sudha, K. M. Narasimhan, V. G. Saraswathy, S. Sankararaman, J. Org. Chem. 1996,61,1877.
[4]a) S. Kulasegaram, R. J. Kulawiec, J. Org. Chem.1997,62,6547; b) S. Kulasegaram, R. Kulawiec, Tetrahedron 1998,54,1361.
[5]X. Deng, X. Sun, Y. Tang, J. Org. Chem.2005,70,6537.
[6]D. K. Nielsen, A. G. Doyle, Angew. Chem. Int. Ed.2011,50,6056.
[7]R. F. Lambert, R. J. Hinkle, S. E. Ammann, Y. Lian, J. Liu, S. E. Lewis, R. D. Pike, J. Org. Chem.2011,76,9269.
[8]a) K. A. Bhatia, K. J. Eash, N. M. Leonard, M. C. Oswald, R. S. Mohan, Tetrahedron let.2001,42,8129; b) M. W. C. Robinson, K. S. Pillinger, A. E. Graham, Tetrahedron let.2006,47,5919; c) M. W. C. Robinson, K. S. Pillinger, I. Mabbett, D. A. Timms, A. E. Graham, Tetrahedron 2010,66,8377.
[9]E. J. Corey, M. Chaykovsky, J. Am. Chem. Soc.1965,87,1353.
[10]a) S. Pedragosa-Moreau, C. Morisseau, J. Zylber, A. Archelas, J. Baratti, R. Furstoss, J. Org. Chem.1996,61,7402; b) H. Jin, Z. Li, X. Dong, Org. Biomol. Chem.2004,2,408; c) S. A. Kavanagh, A. Piccinini, E. M. Fleming, S. J. Connon, Org. Biomol. Chem.2008,6,1339; and reference 6.
[1]For leading reviews on ylide reactions, please see: a) E. M. McGarrigle, E.L. Myers, O. Ilia, M. A. Shaw, S. L. Riches, V. K. Aggarwal, Chem. Rev. 2007, 107, 5841; b) Y. Tang, S. Ye, X.-L. Sun, Synlett 2005, 2720; c) V. K. Aggarwal, C. L. Winn, Ace. Chew. Res. 2004, 37, 611; d) H. Lebel, J. F. Marcouxv, C. Molinnaro, A. B. Charette, Chem. Rev. 2003, 103, 977; e) L.-X. Dai, X.-L. Hou, Y.-G. Zhou, Pure Appl. Chem. 1999, 71, 369; f) A.-H. Li, L.-X. Dai, V. K. Aggarwal, Chem. Rev. 1997, 97, 2341; g) X.-L. Sun, Y. Tang, Ace. Chem. Res., 2008, 41, 937; h) V. K. Aggarwal, J. Richardson, Chem. Commun. 2003, 2644.
[2]For selected recent references, see: a) M. G. Unthank, N. Hussain, V. K. Aggarwal, Angew. Chem. Int. Ed. 2006, 45, 7066; b) V. K. Aggarwal, E. Grange, Chem. Eur. J. 2006, 12, 568; c) M. G. Unthank, B. Tavassoli, V. K. Aggarwal, Org. Lett. 2008, 10, 1501; d) L.-W. Ye, X.-L. Sun, C. -Y. Li, Y. Tang, J. Org. Chem. 2007, 72, 1335; e) Q.-G. Wang, X.-M. Deng, B.-H. Zhu, L.-W. Ye, X.-L. Sun, C.-Y. Li, C.-Y. Zhu, Q. Shen, Y. Tang, J. Am. Chem. Soc. 2008, 130, 5408; f) Y. Wang, W. Zhang, J. V. Colandrea, L. S. Jimenez, Tetrahedron 1999, 55, 10659; g) K. Kim, L. S. Jimenez, Tetrahedron: Asymmetry 2001, 12, 999, and references therein.
[3]a) J. R. Neff, R. R. Gruetzmacher, J. E. Nordlander, J. Org. Chem. 1974, 39, 3814; b) Y. Tang, Y.-Z. Huang, L.-X. Dai, J. Sun, W. Xia, J. Org. Chem. 1997, 62, 954; c) S. Ye, Z. Huang, C. Xia, Y. Tang, L. Dai, J. Am. Chem. Soc. 2002, 124, 2432; d) X. Deng, P. Cai, S. Ye, X. Sun, W. Liao, K. Li, Y. Tang, Y. Wu, L. Dai, J. Am. Chem. Soc. 2006,128, 9730.
[4]Y. Zhang, Z. Chen, Y. Xiao, J. Zhang, Chem. Eur. J. 2009, 15, 5208.
[5]a) Y. Xiao, J. Zhang, Angew. Chem. Int. Ed. 2008, 47, 1903; b) X. Yu, H. Ren, Y. Xiao, J. Zhang, Chem. Eur. J. 2008, 14, 8481; c) L. Fan, W. Zhao, W. Jiang, J. Zhang, Chem. Eur. J. 2008, 14, 9139.
[6]a) J. A. Monn, M. J. Valli, S. M. Massey, R. A. Wright, C. R. Salhoff, B. G. Johnson, T. Howe, C. A. Alt, G. A. Rhodes, R. J. Robey, K. R. Griffey, J. P. Tizzano, M. J. Kallman, D. R. Helton, D. D. Schoepp, J. Med. Chem. 1997, 40, 528; b) H. O. Bertrand, A. S. Bessis, J. P. Pin, F. C. Acher, J. Med. Chem. 2002, 45,3171; c) G. Yue, L. Yang, C. Yuan, X. Jiang, B. Liu, Org. Lett.2011,13, 5406; d) Y. Lu, X. Peng, Org. Lett.2011,13,2940.
[7]a) V. Mamane, T. Gress, H. Krause, A. Furstner, J. Am. Chem. Soc.2004,126, 8654; b) Y. Harrak, C. Blaszykowski, M. Bernard, K. Cariou, E. Mainetti, V. Mouries, A. Dhimane,L.Fensterbank, M. Malacria, J. Am. Chem. Soc.2004,126, 8656; c) H. Horie, T. Kurahashi, S. Matsubara, Angew. Chem. Int. Ed.2011,50, 8956; for reviews, see:d) V. Michelet, P. Y. Toullec, J. P. GenTt, Angew. Chem. Int. Ed.2008,47,4268; e) C. Aubert, L. Fensterbank, P. Garcia, M. Malacria, A. Simonneau, Chem. Rev.2011,111,1954.
[8]T. Yao, X. Zhang, R. C. Larock, J. Am. Chem. Soc.2004,126,11164.
[9]M. E. Krafft, J. W. Cran, Synlett 2005,1263.
[10]H. Gershon, L. Shanks, D. E. Gawiak, J. Med. Chem.1916,19,1069.
[1]a) J. I. G. Cadogan, Organophosphorus Reagents in Organic Synthesis, Academic Press:New York,1979; b) R. Bohlmann, In Comprehensive Organic Synthesis, Vol.6, (Eds:B. M. Trost, I. Fleming,) Pergamon:London,1991, Chap.1.7,203; c) R. Sustmann, In Comprehensive Organic Synthesis, Vol.6, (Eds:B. M. Trost, I. Fleming,) Pergamon:London,1991, Chap.2.1,301; c) D. J. Gorin, B. D. Sherry, F. D. Toste, Chem. Rev.2008,108,3351.
[2]a) X. Lu, C. Zhang, Z. Xu, Acc. Chem. Res.2001,34,535; b) D. H. Jr. Valentine, J. H. Hillhouse, Synthesis.2003,317; c) J. L. Methot, W. R. Roush, Adv. Synth. Catal.2004,346,1035; d) X. Lu, Y. Du, C. Lu, Pure. Appl. Chem.2005,77, 1985; e) V. Nair, R. S. Menon, A. R. Sreekanth, N. Abhilash, A. T. Biju, Ace. Chem. Res.2006,39,520; f) L. Ye, J. Zhou, Y. Tang, Chem. Soc. Rev.2008,37, 1140; g) C. E. Aroyan, A. Dermenci, S. J. Miller, Tetrahedron 2009,65,4069; h) Y. Wei, M. Shi, Ace. Chem. Res.2010,43,1005; i) A. Marinetti, A. Voituriez, Synlett 2010,174.
[3]a) C. Zhang, X. Lu, J. Org. Chem.1995,60,2906; b) Z. Xu, X. Lu, Tetrahedron Lett.1997,38,3461; c) Z. Xu, X. Lu, J. Org. Chem.1998,63,5031; d) Z. Xu, X. Lu, Tetrahedron Lett.1999,40,549; e) X. Lu, Z. Lu, X. Zhang, Tetrahedron, 2006,62,457.
[4]a) Y. Du, X. Lu, C. Zhang, Angew. Chem., Int. Ed.,2003,42,1035; b) Y. Du, J. Feng, X. Lu, Org. Lett.,2005,7,1987; c) J. Feng, X. Lu, A. Kong, X. Han, Tetrahedron,2007,63,6035; d) S. Zheng, X. Lu, Org. Lett.,2008,10,4481; e) S. Zheng, X. Lu, Org. Lett.,2009,11,3978; f) S. Zheng, X. Lu, Tetrahedron Lett., 2009,50,4532.
[5]a) Y. Xia, Y. Liang, Y. Chen, M. Wang, L. Jiao, F. Huang, S. Liu, Y. Li, Z. Yu, J. Am. Chem. Soc.2007,129,3470; b) Y. Liang, S. Liu, Y. Xia, Y. Li, Z. Yu, Chem. Eur. J.2008,14,4361.
[6]a) X. Zhu, J. Lan, O. Kwon, J. Am. Chem. Soc.2003,125,4716; b) X. Zhu, A. Schaffner, R. C. Li, O. Kwon, Org. Lett.2005,7,2977; c) E. Mercier, B. Fonovic, C. Henry, O. Kwon, T. Dudding, Tetrahedron Lett.2007,48,3617; d) S. Castellano, H. D. G. Fiji, S. S. Kinderman, M. Watanabe, P. de Leon, F. Tamanoi, O. Kwon, J. Am. Chem. Soc.2007,129,5843.
[7]a) J.-C. Wang, S. S. Ng, M. J. Krische, J. Am. Chem. Soc.2003,125,3682; b) J.-C. Wang, M. J. Krische, Angew. Chem., Int. Ed.2003,42,5855.
[8]a) R. P. Wurz, G. C. Fu, J. Am. Chem. Soc.2005,127,12234; b) J. E. Wilson, G. C. Fu, Angew. Chem., Int. Ed.2006,45,1426.
[9]a) L. Ye, X. Sun, Q. Wang, Y. Tang, Angew. Chem., Int. Ed.2007,46,5951; b) L Ye, X. Han, X. Sun, Y. Tang, Tetrahedron 2008,64,1487; c) X. Han, L.Ye, X. Sun, Y. Tang, J. Org. Chem.2009,74,3394.
[10]a) Y. Xiao, J. Zhang, Adv. Synth. Catal.2009,351,617; b) Y. Xiao, J. Zhang, Chem. Commun.2009,3594; c) F. Liu, J. Zhang, Angew. Chem. Int. Ed.2009,48, 5505; d) W. Li. Y. Li, J. Zhang, Chem. Eur. J.2010,16,6447; e) W. Li, Y. Xiao, J. Zhang, Adv. Synth. Catal.2009,351,3083.