有机催化的多米诺环化反应及oxindole骨架合成方法研究
|
摘要
在第一章里,我们对近来报道的有机催化的多米诺环化反应进行了综述。近年来有机催化的多米诺反应已经迅速地成为有机化学中强有力的工具。越来越多的有机催化的多组分多米诺反应被应用于利用简单的前体在一步反应中高效而又立体选择性的构建复杂分子。它们经常表现出卓越的立体选择性而且对环境非常友好,因为避免了有毒金属的使用。不对称有机催化剂主要分为手性胺和手性Brφnsted酸。手性胺,特别是手性二级胺催化的多米诺反应的报道非常多,因为二级胺既可以以烯胺的形式催化,又可以以亚胺离子的形式催化。大部分手性胺催化的多米诺反应是基于亚胺离子-烯胺活化,烯胺-烯胺活化和烯胺-亚胺离子活化这几种活化方式。在Brφnsted酸催化的多米诺反应中,底物的活化依赖于部分质子化或者与催化剂形成严格定向的氢键。催化剂与底物之间的相互作用是非共价的,手性离子对是实质意义上的活性物种。手性硫脲衍生物和手性磷酸衍生物是有效的Brφnsted酸有机催化剂。我们发展了一种简单易行的,利用脯氨酸催化的苯胺、甲醛和环己酮的Mannich型缩合一锅法高效合成1,3-二芳基-5-螺六氢嘧啶类化合物的方法。在这个一锅法三组分反应中,有六分子参与,有六个新的共价键生成,利用简单易得的原料和催化剂很容易就合成出了双环化合物。
在第二章里,我们对oxindole骨架的合成方法进行了综述。Oxindoles是广泛存在于天然产物和具有生物活性的分子中的重要结构单元。已报道的oxindole合成方法有很多,包括邻氨基苯乙酸和α-卤素或α-羟基乙酰苯氨的环化反应、靛红和吲哚的衍生、自由基环化、钯催化的Heck反应、Heck/氰化反应、氰氨化反应,Csp2和Csp3的偶联、Pummerer反应以及丙炔酰胺和2-(炔基)芳基异氰酸酯的环化。我们发展了两个可靠且操作简单的方法,即α,β-不饱和酰胺在钯催化下的C-H官能化反应和碘鎓离子促进下的亲电环化反应,用以合成官能化的oxindole。
In the first chapter, we have reviewed the recent studies on organocatalytic domino cyclizations. Recently, organocatalytic domino reactions have quickly become a powerful and efficient tool in organic chemistry. More and more organocatalytic multicomponent domino reactions have been utilized for the efficient and stereoselective construction of complex molecules from simple precursors in a single process, and they often proceed with excellent stereoselectivities and are environmentally friendly because the use of toxic metals are avoided. Asymmetric organocatalysts mainly consist of chiral amines and chiral Brφnsted acids. Organocatalytic domino reactions catalyzed by amines, especially secondary amines, are widespread, as secondary amines are capable of both enamine and iminium catalysis. Most of the chiral amines-catalyzed domino reactions are based on iminium-enamine activation, enamine- enamine activation and enamine- iminium activation. In Brφnsted acids-catalyzed domino reactions, the activation of the substrate relies on the partial protonation or the formation of a strictly directed hydrogen bond by the catalyst. The interaction between the catalyst and the substrate is noncovalent, and the chiral ion pair is the intrinsic activated species. Chiral thiourea-based derivatives and phosphoric acid derivatives are effective Brφnsted acid organocatalysts. We have developed a facile and efficient synthesis of 1,3-diaryl-5-spirohexahydropyrimidines via a one-pot Mannich-type condensation of anilines, formaldehyde and cyclohexanones catalyzed by proline. In this one-pot three-component reaction, six molecules of reactants are involved and six new covalent bonds are generated. Bicyclic products are obtained from the starting materials in one pot using readily available starting materials and catalysts.
In the second chapter, we have reviewed methodology for the synthesis of oxindole skeleton. Oxindoles are common and important substructures in natural products and biologically active molecules. Numerous methods have been reported for the synthesis of oxindoles, including cyclization of o-aminophenylacetic acids andα-halo orα-ahydroxy acetanilides, the derivatization of isatin and indoles, radical cyclizations, palladiumcatalyzed Heck reactions, domino Heck/cyanation reactions, cyanoamidation reactions, Coupling of Csp2 and Csp3, Pummerer reaction, and cyclization of propiolanilides and 2-(alkynyl)aryl isocyanates. We have developed two reliable and operationally simple protocols to synthesize functionalized oxindoles via palladium-Catalyzed C-H functionalization and iodonium-mediated electrophilic cyclization of simpleα,β-unsaturated amides.
在第二章里,我们对oxindole骨架的合成方法进行了综述。Oxindoles是广泛存在于天然产物和具有生物活性的分子中的重要结构单元。已报道的oxindole合成方法有很多,包括邻氨基苯乙酸和α-卤素或α-羟基乙酰苯氨的环化反应、靛红和吲哚的衍生、自由基环化、钯催化的Heck反应、Heck/氰化反应、氰氨化反应,Csp2和Csp3的偶联、Pummerer反应以及丙炔酰胺和2-(炔基)芳基异氰酸酯的环化。我们发展了两个可靠且操作简单的方法,即α,β-不饱和酰胺在钯催化下的C-H官能化反应和碘鎓离子促进下的亲电环化反应,用以合成官能化的oxindole。
In the first chapter, we have reviewed the recent studies on organocatalytic domino cyclizations. Recently, organocatalytic domino reactions have quickly become a powerful and efficient tool in organic chemistry. More and more organocatalytic multicomponent domino reactions have been utilized for the efficient and stereoselective construction of complex molecules from simple precursors in a single process, and they often proceed with excellent stereoselectivities and are environmentally friendly because the use of toxic metals are avoided. Asymmetric organocatalysts mainly consist of chiral amines and chiral Brφnsted acids. Organocatalytic domino reactions catalyzed by amines, especially secondary amines, are widespread, as secondary amines are capable of both enamine and iminium catalysis. Most of the chiral amines-catalyzed domino reactions are based on iminium-enamine activation, enamine- enamine activation and enamine- iminium activation. In Brφnsted acids-catalyzed domino reactions, the activation of the substrate relies on the partial protonation or the formation of a strictly directed hydrogen bond by the catalyst. The interaction between the catalyst and the substrate is noncovalent, and the chiral ion pair is the intrinsic activated species. Chiral thiourea-based derivatives and phosphoric acid derivatives are effective Brφnsted acid organocatalysts. We have developed a facile and efficient synthesis of 1,3-diaryl-5-spirohexahydropyrimidines via a one-pot Mannich-type condensation of anilines, formaldehyde and cyclohexanones catalyzed by proline. In this one-pot three-component reaction, six molecules of reactants are involved and six new covalent bonds are generated. Bicyclic products are obtained from the starting materials in one pot using readily available starting materials and catalysts.
In the second chapter, we have reviewed methodology for the synthesis of oxindole skeleton. Oxindoles are common and important substructures in natural products and biologically active molecules. Numerous methods have been reported for the synthesis of oxindoles, including cyclization of o-aminophenylacetic acids andα-halo orα-ahydroxy acetanilides, the derivatization of isatin and indoles, radical cyclizations, palladiumcatalyzed Heck reactions, domino Heck/cyanation reactions, cyanoamidation reactions, Coupling of Csp2 and Csp3, Pummerer reaction, and cyclization of propiolanilides and 2-(alkynyl)aryl isocyanates. We have developed two reliable and operationally simple protocols to synthesize functionalized oxindoles via palladium-Catalyzed C-H functionalization and iodonium-mediated electrophilic cyclization of simpleα,β-unsaturated amides.
引文
1. a) R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994; b) Comprehensive Asymmetric Catalysis (Ed.:E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin,1999; c) Catalytic Asymmetric Synthesis,2nd ed. (Ed.:I. Ojima), Wiley-VCH, New York,2000; d) Transition Metals for Organic Synthesis,2nd ed. (Eds.:M. Beller, C. Bolm), Wiley-VCH, Weinheim,2004.
2. a) Biocatalysts for Fine Chemicals Synthesis (Ed.:S. M. Roberts), Wiley-VCH, New York,1999; b) Enzyme Catalysis in Organic Synthesis,2nd ed. (Eds.:K. Drauz, H. Waldmann), Wiley-VCH, Weinheim,2002; c) A. S. Bommarius, B. R. Riebel, Biocatalysis, Wiley-VCH, Weinheim,2004.
3. a) P. I. Dalko, L. Moisan, Angew. Chem. Int. Ed.2001,40,3726; b) B. List, Synlett 2001,1675; c) B. List, Tetrahedron 2002,58,2481; d) P. I. Dalko, L. Moisan, Angew. Chem. Int. Ed.2004,43,5138; e) A. Berkessel, H. Groger, Asymmetric Organocatalysis, Wiley-VCH,Weinheim,2005; f) J. Seayad, B. List, Org. Biomol. Chem. 2005, 3, 719; g) G. Lelais, D. W. C. MacMillan, Aldrichimica Acta 2006,39,79.
4. a) D. Enders, C. Grondal, M. R. M. Hiittl,1590-1601; Angew. Chem. Int. Ed. 2007,46,1570; b) B. Westermann, M. Ayaz, S. S. van Berkel, Angew. Chem. Int. Ed.2010,49,846.
5. a) B. List, Chem. Commun.2006,819, and references therein; b) K. A. Ahrendt, C. J. Borth, D. W. C. MacMillan, J. Am. Chem. Soc.2000,122,4243; c) A. B. Northrup, D.W. C. MacMillan, J. Am. Chem. Soc.2002,124,2458.
6. T. Bui, C. F. Barbas Ⅲ, Tetrahedron Lett.2000,41,6951.
7. For a similar approach, see:D. Rajagopal, R. Narayanan, S. Swaminanthan, Tetrahedron Lett.2001,42,4887.
8. a) U. Eder, G. Sauer, R. Wiechert, Angew. Chem. Int. Ed. Engl.1971,10,496; b) Z. G. Hajos, D. R. Parrish, J. Org. Chem.1974,39,1615.
9. N. Halland, P. S. Aburel, K. A. Jφgensen, Angew. Chem. Int. Ed.2004,43,1272.
10. a) J. Pulkkinen, P. S. Aburel, N. Hallend, K. A. Jφgensen, Adv. Synth. Catal.2004, 346,1077; b) D. Gryko, Tetrahedron: Asymmetry 2005,16,1377.
11. W. Wang, H. Li, J. Wang, L. Zu, J. Am. Chem. Soc.2006,128,10354.
12. a) T. Govender, L. Hojabri, F. M. Maghaddam, P. I. Arvidsson, Tetrahedron: Asymmetry 2006,17,1763; b) H. Li, J. Wang, T. E-Nunu, L.-S. Zu, W. Jiang, S.-H. Wei, W. Wang, Chem. Commun.2007,507; c) H. Sunden, I. Ibrahem, G.-L Zhao, L. Eriksson, A. Cordova, Chem. Eur. J.2007,13,574.
13. a) H. Sunden, R. Rios, I. Ibrahem, G.-L. Zhao, L. Eriksson, A. Cordova, Adv. Synth. Catal.2007,349,827; b) H. Li, J. Wang, H. Xie, L. Zu, W. Jiang, E. N. Duesler, W. Wang, Org. Lett.2007,9,965.
14. S. Brandau, E. Maerten, K. A. Jφgensen, J. Am. Chem. Soc.2006,128,14986.
15. J. L. Vicario, S. Reboredo, D. Badia, L. Carrillo, Angew. Chem. Int. Ed.2007,46, 5168.
16. L. Zu, H. Li, H. Xie, J. Wang, W. Jiang, Y. Tang, W. Wang, Angew. Chem. Int. Ed.2007,46,3732.
17. J. Wang, H. Li, H. Xie, L. Zu, X. Shen, W. Wang, Angew. Chem. Int. Ed.2007, 46,9050.
18. a) N. S. Chowdari, D. B. Ramachary, A. Cordova, C. F. Barbas III, Tetrahedron Lett.2002,43,9591; b) A. Cordova, Tetrahedron Lett.2004,45,3949; c) J. Casas, M. Engquist, I. Ibrahem, B. Kaynak, A. Cordova, Angew. Chem. Int. Ed. 2005,44,1343; d) E. Reyes, A. Cordova, Tetrahedron Lett.2005,46,6605; c) A. Cordova, M. Engquist, I. Ibrahem, J. Casa, H. Sunden, Chem. Commun.2005, 2047.
19. D. Enders, C. Wang, J. W. Bats, Angew. Chem. Int. Ed.2008,47,7539.
20. T. Itoh, M. Yokoya, K. Miyauchi, K. Nagata, A. Ohsawa, Org. Lett.2003,5, 4301.
21. L.-Y. Wu, G. Bencivenni, M. Mancinelli, A. Mazzanti, G. Bartoli, P. Melchiorre, Angew. Chem. Int. Ed.2009,48,7196.
22. G. Bencivenni, L.-Y. Wu, A. Mazzanti, B. Giannichi, F. Pesciaioli, M.-P. Song, G. Bartoli, P. Melchiorre, Angew. Chem. Int. Ed.2009,48,7200.
23. For proline-catalyzed a-aminohydroxylation reactions, see:a) G. Zhong, Angew. Chem. Int. Ed.2003,42,4247; b) S. P. Brown, M. P. Brochu, C. J. Sinz, D.W. C. MacMillan, J. Am. Chem. Soc.2003,125,10808; c) Y. Hayashi, J. Yamaguchi, K. Hibino, M. Shoji, Tetrahedron Lett.2003,44,8293.
24. Y. Yamamoto, N. Momiyama, H. Yamamoto, J. Am. Chem. Soc.2004,126, 5962.
25. H. Sunden, I. Ibrahem, L. Eriksen, A. Cordova, Angew. Chem. Int. Ed.2005,44, 4877.
26. H. Yang, R. G. Carter, J. Org. Chem.2009,74,5151.
27. D. Enders, M. R. M. Huttl, C. Grondal, G. Raabe, Nature 2006,441,861.
28. D. Enders, M. R. M. Huttl, J. Runsink, G. Raabe, B. Wendt, Angew. Chem. Int. Ed.2007,46,467.
29. A. Carlone, S. Cabrera, M. Marigo, K. A. Jφgensen, Angew. Chem. Int. Ed.2007, 46,1101.
30. D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Angew. Chem. Int. Ed.2003, 42,4233.
31. D. B. Ramachary, C. F. Barbas Ⅲ, Chem. Eur. J.2004,10,5323. For further extensions, see:D. B. Ramachary, K. Anebousely, N. S. Chowdary, C. F. Barbas Ⅲ, J. Org. Chem.2004,69,5838.
32. Y.-K. Liu, C. Ma, K. Jiang, T.-Y. Liu, Y.-C. Chen, Org. Lett.2009,11,2848.
33. M. Marigo, S.Bertelsen, A. Landa, K. A. Jφgensen, J. Am. Chem. Soc.2006,128, 5745.
34. Y. Hayashi, T. Okano, S. Aratake, D. Hazelard, Angew. Chem. Int. Ed.2007,46, 4922.
35. E. Reyes, H. Jiang, A. Milelli, P. Elsner, R. G. Hazell, K. A. Jogensen, Angew. Chem. Int. Ed.2007,46,9202.
36. W. Chen, W. Du, Y.-Z. Duan, Y. Wu, S.-Y. Yang, Y.-C. Chen, Angew. Chem. Int. Ed.2007,46,7667.
37. B. Han, J.-L. Li, C. Ma, S.-J. Zhang, Y.-C. Chen, Angew. Chem. Int. Ed.2008,47, 9971.
38. B. Han, Z.-Q. He, J.-L. Li, R. Li, K. Jiang, T.-Y. Liu, Y.-C. Chen, Angew. Chem. Int. Ed.2009,48,5474.
39. S. Cabrera, J. Aleman, P. Bolze, S. Bertelsen, K. A. Jφgensen, Angew. Chem. Int. Ed.2008,47,121.
40. a)Y. Huang, A. M. Walji, C. H. Larsen, D. W. C. MacMillan, J. Am. Chem. Soc. 2005,127,15051; b) B. Simmons, A. M.Walji, D. W. C.MacMillan, Angew. Chem., Int. Ed.2009,48,4349; c) Y. Wang, D.-F. Yu, Y.-Z. Liu, H. Wei, Y.-C. Luo, D. J. Dixon, P.-F. Xu, Chem. Eur. J.2010,16,3922.
41. S. P. Lathrop, T. Rovis, J. Am. Chem. Soc.2009,131,13628.
42. For reviews, see:a) P. R. Schreiner, Chem. Soc. Rev.2003,32,289; b) P. M. Pihko, Angew. Chem. Int. Ed.2004,43,2062; c) C. Bolm, T. Rantanen, I. Schiffers, L. Zani, Angew. Chem. Int. Ed.2005,44,1785; d) M. S. Taylor, E. N. Jacobsen, Angew. Chem. Int. Ed.2006,45,1520; e) S. J. Connon, Angew. Chem. Int. Ed.2006,45,3909; f) T. Akiyama, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2006,348,999.
43. a) Y. Hoashi, T. Yabuta, Y. Takemoto, Tetrahedron Lett.2004,45,9185; b)Y. Hoashi, T. Yabuta, P. Yuan, H. Miyabe, Y. Takemoto, Tetrahedron 2006,62, 365.
44. M. Rueping, C. Azap, Angew. Chem. Int. Ed.2006,45,7832.
45. J. Seayad, A. M. Seayad, B. List, J. Am. Chem. Soc.2006,128,1086.
46. J. Itoh, K. Fuchibe, T. Akiyama, Angew. Chem. Int. Ed.2006,45,4796.
47. M. Rueping A. P. Antonchick, Angew. Chem. Int. Ed.2008,47,5836.
48. J. Zhou, B. List, J. Am. Chem. Soc.2007,129,7498.
49. M. Rueping, A. P. Antonchick, E. Sugiono, K. Grenader, Angew. Chem. Int. Ed. 2009,48,908.
50. H. Liu, G. Dagousset, G. Masson, P. Retailleau, J. Zhu, J. Am. Chem. Soc.2009, 131,4598.
51. a) H. Finch, E. A. Peterson, S. A. Ballard, J. Am. Chem. Soc.1952,74,2016; b) R. F. Evans, Aust. J. Chem.1967,20,1643; c) C. Jutz, A. F. Kirschner, R.-M. Wagner, Chem. Ber.1977,110,1259; d) I. A. Perillo, M. B. Garcia, J. A. Bisceglia, L. R. Orelli, J. Heterocycl. Chem.2002,39,655; e) A. R. Katrizky, S. K. Singh, H.-Y. He, J. Org. Chem.2002,67,3115.
52. a) M. Mayr, M. R.Buchmeiser, Macomol. Rapid Commun.2004,25,231; b) M. Mayr, K.Wurst, K.-H.Ongania, M. R.Buchmeiser, Chem. Eur. J.2004,10,1256.
53. a) I. Ibrahem, J. Casas, A. Cordova, Angew. Chem., Int. Ed.2004,43,6528; b) I. Ibrahem, W. Zou, J. Casas, H. Sunden, A. Cordova, Tetrahedron 2006,62,357.
1. a) A. Jossang, P. Jossang,H. A. Hadi, T. Sevenet, B. Bodo, J. Org. Chem.1991, 56,6527; b) R. Thericke, Y. Q. Tang, I. Sattler, S. Grabley, X. Z. Feng, Eur. J. Org. Chem.2001,261; c) C. Marti, E. M. Carreira, Eur. J. Org. Chem.2003, 2209; d) M. Tsuda, T. Mugishima, K. Komatzu, T. Sone, M. Tanaka, Y. Mikaimi, M. Shiro, M. Hirai, Y. Ohizumii, J. Kobayashi, Tetrahedron Lett.2003,59,3227; e) C. V. Galliford, K. A. Scheidt, Angew. Chem. Int. Ed.2007,46,8748; f) J. S. Bindra, in:The Alkaloids (Ed.:R. H. F. Manske), Academic Press, New York, 1973, vol.14, pp.84-121. g) X. Zhang, C. D. Smith, Mol. Pharmacol.1996,49, 288.
2. R. J. Sundberg, Indoles, Academic Press, London,1996, pp.17,152-154.
3. a) A. H. Beckett, R. W. Daisley, J. Walker, Tetrahedron 1968,24,6093, and references therein; b) D. Ben-Ishai, N. Peled, I. Sataty, Tetrahedron Lett.1980, 21,569.
4. a) R. M. Acheson, J. M. Vernon and R. W. Snaith, J. Chem. Soc.,1964,3229; b) J. M. Muchowski, Can. J. Chem.,1970,48,422; c) A.Walser, J. F. Blount and R. I. Fryer, J. Org. Chem.,1973,38,3077.
5. a) N. Finch and W. I. Taylor, J. Am. Chem. Soc.,1962,84,3871; b) K. V. Lichman, J. Chem. Soc. C,1971,2539.
6. M. Ito, C. W. Clark, M. Mortimore, J. B. Goh and S. F. Martin, J. Am. Chem. Soc.,2001,123,8003.
7. A. Bischler, B. Napiralsky, Ber. Dtsch. Chem. Ges.1893,26,1903.
8. a) N. Finch, W. I. Taylor, J. Am. Chem. Soc.1962,84,1318; b) N. Finch, W. I. Taylor, J. Am. Chem. Soc.1962,84,3871.
9. a) S. F. Martin, M. Mortimore, Tetrahedron Lett.1990,31,4557; b) S. F. Martin, B.; Benage, L. S. Geraci, J. E. Hunter, M. Mortimore, J. Am. Chem. Soc.1991, 113,6161.
10. A. Deiters, M. Petterson, S. F. Martin, J. Org. Chem.,2006,71,6547.
11. a) C. Pellegrini, C. Strassler, M. Weber, H. J. Borschberg, Tetrahedron: Asymmetry 1994,5,1979; b) C. Pellegrini, M. Weber, H. J. Borschberg, Helv. Chim. Acta 1996,79,151.
12. a) S. D. Edmondson, S. J. Danishefsky, Angew. Chem. Int. Ed.1998,37,1138;b) S. D. Edmondson, S. J. Danishefsky, L. Sepp-Lorenzino, N. Rosen, J. Am. Chem. Soc.1999,121,2147.
13. H. S. Wang, A. Ganesan, J. Org. Chem.2000,65,4685.
14. M. Somei, K. Noguchi, R. Yamagami, Y. Kawada, K. Yamada, F. Yamada, Heterocycles 2000,53,7.
15. N. Finch, I. H. C. Hsu, C. W. Gemenden, W. I. Taylor, J. Am.Chem. Soc.1963, 85,1520.
16. A. Jossang, P. Jossang, H. A. Hadi, T. Sevenet, B. Bodo, J.Org. Chem.1991,56, 6527.
17. a) A. C. Peterson, J. M. Cook, Tetrahedron Lett.1994,35,2651; b) A. C. Peterson, J. M. Cook, J. Org. Chem.1995,60,120.
18. a) P. Yu, J. M. Cook, J. Org. Chem.1998,63,9160; b) P. Yu, T. Wang, J. Li, J. M. Cook, J. Org. Chem.2000,65,3173; c) X. Z. Wearing, J. M. Cook, Org. Lett. 2002,4,4237.
19. M. Lachia, C. Poriel, A. Z. Slawin, Christopher J. Moody, Chem. Commun.2007, 286.
20. I. D. Hills, G. C. Fu, Angew. Chem. Int. Ed.2003,42,3921.
21. T. Sawada, D. E. Fuerst, J. L. Wood, Tetrahedron Lett.2003,44,4919.
22. B. M. Trost, M. K. Brennan, Org. Lett.2006,8,2027.
23. H. Miyamoto, Y. Okawa, A. Nakazaki, S. Kobayashi, Angew. Chem. Int. Ed. 2006,45,2274.
24. H. Miyamoto, Y. Okawa, A. Nakazaki, S. Kobayashi, Tetrahedron Lett.2007,48, 1805.
25. a) J.-F. Carpentier, A. Morteux, Tetrahedron: Asymmetry 1997,8,1083; b) K. Funabashi, M. Jachmann, M. Kanai, M. Shibasaki, Angew. Chem. Int. Ed.2003, 42,5489; c) G. Luppi, P. G. Cozzi, M. Monari, B. Kaptein, Q. B. Broxterman, C. Tomasini, J. Org. Chem.2005,70,7418; d) G. Chen, Y. Wang, H. He, S. Gao, X. Yang, X. Hao, Heterocycles 2006,68,2327; e) G. Luppi, M. Monari, R. J. Correa, F. A. Violante, A. C. Pinto, B. Kaptein, Q. B. Broxterman, S. J. Garden, C. Tomasini, Tetrahedron 2006,62,12017; f) M. Kitajima, I. Mori, K. Arai, N. Kogure, H.mTakayama, Tetrahedron Lett.2006,47,3199; g) B Alcaide, P. Almendros, R. Rodriguez-Acebes, J. Org. Chem.2006,71,2346; h) A. V. Malkov, M. A. Kabeshov, M. Bella, O. Kysilka, D. A. Malyshev, K. Pluhackova, P. Kocovsky, Org. Lett.2007,9,5473; i) J.-R. Chen, X.-P. Liu, X.-Y. Zhu, L. Liang, Y.-F. Qiao, J.-M. Zhang, W.-J. Xiao, Tetrahedron 2007,63,10437; j) R. J. Correa, S. J. Garden, G. Angelici, C. Tomasini, Eur. J. Org. Chem.2008,736; k) S. Nakamura, N. Hara, H. Nakashima, K. Kubo, N. Shibata, T. Toru, Chem. Eur. J. 2008,14,8079; 1) H. Lai, Z. Huang, Q. Wu, Y. Qin, J. Org. Chem.2009,74, 283.
26. K. C. Nicolaou, P. B. Rao, J. Hao, M. V. Reddy,G. Rassias, X. Huang, D. Y.-K. Chen, S. A. Snyder, Angew. Chem. Int. Ed.2003,42,1753.
27. R. Shintani, M. Inoue, T. Hayashi, Angew. Chem. Int. Ed.2006,45,3353.
28. P. Y. Toullec, R. B. C. Jagt, J. G. De Vries, B. L. Feringa, A. J. Minnaard, Org. Lett.2006,8,2715.
29. J. Itoh, S. B. Han, M. J. Krische, Angew. Chem. Int. Ed.2009,48,6313.
30. a) I. S. Kim, M.-Y. Ngai, M. J. Krische, J. Am. Chem. Soc.2008,130,14891; b) I. S. Kim, S. B. Han, M. J. Krische, J. Am. Chem. Soc.2009,131,2514.
31. N. V. Hanhan, A. H. Sahin, T. W. Chang, J. C. Fettinger, A. K. Franz, Angew. Chem. Int. Ed.2010,49,744.
32. V. Nair, S. Vellalath, M. Poonoth, R. Mohan, E. Suresh, Org. Lett.2006,8,507.
33. D. Basavaiah, K, R, Reddy, Org. Lett.2007,9,57.
34. V. Schulz, M. Davoust, M. Lemarie, J-F Lohier, J. S. de Santos, P. Metzner, J-F. Briere, Org. Lett.2007,9,1745.
35. D. Basavaiah, J. S. Rao, R. J. Reddy, A. J. Rao, Chem. Commun.,2005,2621.
36. K. Jones, J. Wilkinson,J. Chem. Soc., Chem. Commun.1992,1767.
37. J. Cossy, M. Cases, D. G.Pardo, Tetrahedron Lett.1998,39,2331.
38. S. T. Hilton, T. C. T. Ho, G. Pljevaljcic, K. Jones, Org. Lett.2000,2,2639.
39. a) C. Escolano,K. Jones, Tetrahedron Lett.2000,41,8951; b) C. Escolano, K. Jones, Tetrahedron 2002,58,1453.
40. D. Lizos, R. Tripoli, J. A. Murphy, Chem. Commun.2001,2732.
41. a) M. M. Abelman, T. Oh, L. E. Overman, J. Org. Chem.1987,52,4130; b) A. Ashimori, L. E. Overman, J. Org. Chem.1992,57,4571; c) A. Ashimori, B. Bachand, L. E. Overman, D. J. Poon, J. Am. Chem. Soc.1998,120,6477; d) A. Ashimori, B. Bachand, M. A. Calter, S. P. Govek, L. E. Overman, D. J. Poon, J. Am. Chem. Soc.1998,120,6488.
42. a) W. G. Earley, T. Oh, L. E. Overman, Tetrahedron Lett.1988,29,3785; b) A. Madin, C. J. O'Donnell, T. Oh, D. W. Old, L. E. Overman, M. J. Sharp, Angew. Chem. Int. Ed.1999,38,2934; c) W. G. B. Beyersbergen van Henegouwen, R. M. Fieseler, F. Rutjes, H. Hiemstra, Angew. Chem. Int. Ed.1999,38,2214; d) W. G. B. Beyersbergen van Henegouwen, R. M. Fieseler, F. Rutjes, H. Hiemstra, J. Org. Chem.2000,65,8317.
43. a) A. B. Dounay, K. Hatanaka, J. J. Kodanko, M. Oestreich, L. E. Overman, L. A. Pfeifer, M. M. Weiss, J. Am. Chem. Soc.2003,125,6261; b) A. Huang, J. J. Kodanko, L. E. Overman, J. Am. Chem. Soc.2004,126,14043.
44. L. E. Overman, M. D. Rosen, Angew. Chem. Int. Ed.2000,39,4596.
45. P. Liu, J. H. Seo, S. M. Weinreb, Angew. Chem. Int. Ed.2010,49,2000.
46. R. T. Ruck, M. A. Huffman, M. M. Kim, M. Shevlin, W. V. Kandur, Ian W. Davies, Angew. Chem. Int. Ed.2008,47,4711.
47. A. Pinto, Y. Jia, L. Neuville, J. Zhu, Chem. Eur. J.2007,13,961.
48. a) K. H. Shaughnessy, B. C. Hamann, J. F. Hartwig, J. Org. Chem.1998,63, 6546; b) S. Lee, J. F. Hartwig, J. Org. Chem.2001,66,3402.
49. a) R. Freund, W. W. K. R. Mederski, Helv. Chim. Acta.2000,83,1247; b) T. Y. Zhang, H. Zhang, Tetrahedron Lett.2002,43,193; c) T. Y.; Zhang, H. Zhang, Tetrahedron Lett.2002,43,1363; d) G. C. Bignan, K. Battista, P. J. Connolly, M. J. Orsini, J. Liu, S. A. Middleton, B. A. Reitz, Bioorg. Med. Chem. Lett.2005,15, 5022; e) S. P. Marsden, E. L.Watson, S. A. Raw, Org. Lett.2008,10,2905; f) J. M. Hillgren, S. P. Marsden, J. Org. Chem.2008,73,6459; g) L. Ackermann, R. Vicente, N. Hofmann, Org. Lett.2009,11, 4274.
50. a) F. Glorius, G. Altenhoff, R. Goddard, C. Lehmann, Chem. Commun.2002, 2704; b) T. Arao, K. Kondo, T. Aoyama, Tetrahedron Lett.2006,47,1417; c) E. P. Kundig, T. M. Seidel, Y.-X. Jia, G. Bernardinelli, Angew. Chem. Int. Ed.2007, 46,8484; d) Y.-X. Jia, J. M. Hillgren, E. L. Watson, S. P. Marsden, E. P. Kundig, Chem. Commun.2008,4040.
51. W. Erb, L. Neuville, J. Zhu, J. Org. Chem.2009,74,3109.
52. E. J. Hennessy, S. L. Buchwald, J. Am. Chem. Soc.2003,125,12084.
53. Y.-X. Jia, E. P. Kundig, Angew. Chem. Int. Ed.2009,48,1636.
54. A. Perry, R. J. K. Taylor, Chem. Commun.,2009,3249.
55. L. A. McAllister, S. Brand, R. de Gentile, D. J. Procter, Chem. Commun.,2003, 2380.
56. a) L. A. McAllister, R. A. McCormick, S. Brand, D. J. Procter, Angew. Chem. Int. Ed.2005,44,452; b) M. Miller, W. Tsang, A. Merritt, D. J. Procter, Chem. Commun.,2007,498.
57. W. S. Cheung, R. J. Patch, M. R. Player, J. Org. Chem.2005,70,3741.
58. R. Yanada, S. Obika, T. Inokuma, K. Yanada, M. Yamashita, S. Ohta, Y. Takemoto, J. Org. Chem.2005,70,6972.
59. R. Yanada, S. Obika, M. Oyama, Y. Takemoto, Org. Lett.2004,6,2825.
60. R. Shintani, T. Yamagami, T. Hayashi, Org. Lett.2006,8,4799.
61. D. M. D’Souza, F. Rominger, T. J. J. Muller, Angew. Chem. Int. Ed.2005,44, 153.
62. T.-S. Jiang, R.-Y. Tang, X.-G. Zhang, X.-H. Li, J.-H. Li, J. Org. Chem.2009,74, 8834.
63. a) A. Pinto, L. Neuville, P. Retailleu, J. Zhu, Org. Lett.2006,8,4927; b) A. Pinto, L. Neuville, J. Zhu, Angew. Chem. Int. Ed.2007,46,3291.
64. a) S.Tang, P. Peng, S.-F. Pi, Y. Liang, N.-X. Wang, J.-H. Li, Org. Lett.2008,10, 1179; b) S.Tang, P. Peng, Z.-Q. Wang, B.-X. Tang, C.-L. Deng, J.-H. Li, P. Zhong, N.-X. Wang, Org. Lett.2008,10,1875.
65. S. Kamijo, Y. Sasaki, C. Kanazawa, T. Schuβler, Y. Yamamoto, Angew. Chem. Int. Ed.2005,44,7718.
66. T. Miura, T. Toyoshima, Y. Takahashi, M. Murakami, Org. Lett.2009,11,2141.
67. T. Miura, Y. Takahashi, M. Murakami, Org. Lett.2007,9,5075.
68. S. Jaegli, J.-P. Vors, L. Neuville, J. Zhu, Synlett 2009,2997.
69. S. Jaegli, W. Erb, P. Retailleau, J.-P. Vors, L. Neuville, J. Zhu, Chem. Eur. J. 2010,16,5863.
2. a) Biocatalysts for Fine Chemicals Synthesis (Ed.:S. M. Roberts), Wiley-VCH, New York,1999; b) Enzyme Catalysis in Organic Synthesis,2nd ed. (Eds.:K. Drauz, H. Waldmann), Wiley-VCH, Weinheim,2002; c) A. S. Bommarius, B. R. Riebel, Biocatalysis, Wiley-VCH, Weinheim,2004.
3. a) P. I. Dalko, L. Moisan, Angew. Chem. Int. Ed.2001,40,3726; b) B. List, Synlett 2001,1675; c) B. List, Tetrahedron 2002,58,2481; d) P. I. Dalko, L. Moisan, Angew. Chem. Int. Ed.2004,43,5138; e) A. Berkessel, H. Groger, Asymmetric Organocatalysis, Wiley-VCH,Weinheim,2005; f) J. Seayad, B. List, Org. Biomol. Chem. 2005, 3, 719; g) G. Lelais, D. W. C. MacMillan, Aldrichimica Acta 2006,39,79.
4. a) D. Enders, C. Grondal, M. R. M. Hiittl,1590-1601; Angew. Chem. Int. Ed. 2007,46,1570; b) B. Westermann, M. Ayaz, S. S. van Berkel, Angew. Chem. Int. Ed.2010,49,846.
5. a) B. List, Chem. Commun.2006,819, and references therein; b) K. A. Ahrendt, C. J. Borth, D. W. C. MacMillan, J. Am. Chem. Soc.2000,122,4243; c) A. B. Northrup, D.W. C. MacMillan, J. Am. Chem. Soc.2002,124,2458.
6. T. Bui, C. F. Barbas Ⅲ, Tetrahedron Lett.2000,41,6951.
7. For a similar approach, see:D. Rajagopal, R. Narayanan, S. Swaminanthan, Tetrahedron Lett.2001,42,4887.
8. a) U. Eder, G. Sauer, R. Wiechert, Angew. Chem. Int. Ed. Engl.1971,10,496; b) Z. G. Hajos, D. R. Parrish, J. Org. Chem.1974,39,1615.
9. N. Halland, P. S. Aburel, K. A. Jφgensen, Angew. Chem. Int. Ed.2004,43,1272.
10. a) J. Pulkkinen, P. S. Aburel, N. Hallend, K. A. Jφgensen, Adv. Synth. Catal.2004, 346,1077; b) D. Gryko, Tetrahedron: Asymmetry 2005,16,1377.
11. W. Wang, H. Li, J. Wang, L. Zu, J. Am. Chem. Soc.2006,128,10354.
12. a) T. Govender, L. Hojabri, F. M. Maghaddam, P. I. Arvidsson, Tetrahedron: Asymmetry 2006,17,1763; b) H. Li, J. Wang, T. E-Nunu, L.-S. Zu, W. Jiang, S.-H. Wei, W. Wang, Chem. Commun.2007,507; c) H. Sunden, I. Ibrahem, G.-L Zhao, L. Eriksson, A. Cordova, Chem. Eur. J.2007,13,574.
13. a) H. Sunden, R. Rios, I. Ibrahem, G.-L. Zhao, L. Eriksson, A. Cordova, Adv. Synth. Catal.2007,349,827; b) H. Li, J. Wang, H. Xie, L. Zu, W. Jiang, E. N. Duesler, W. Wang, Org. Lett.2007,9,965.
14. S. Brandau, E. Maerten, K. A. Jφgensen, J. Am. Chem. Soc.2006,128,14986.
15. J. L. Vicario, S. Reboredo, D. Badia, L. Carrillo, Angew. Chem. Int. Ed.2007,46, 5168.
16. L. Zu, H. Li, H. Xie, J. Wang, W. Jiang, Y. Tang, W. Wang, Angew. Chem. Int. Ed.2007,46,3732.
17. J. Wang, H. Li, H. Xie, L. Zu, X. Shen, W. Wang, Angew. Chem. Int. Ed.2007, 46,9050.
18. a) N. S. Chowdari, D. B. Ramachary, A. Cordova, C. F. Barbas III, Tetrahedron Lett.2002,43,9591; b) A. Cordova, Tetrahedron Lett.2004,45,3949; c) J. Casas, M. Engquist, I. Ibrahem, B. Kaynak, A. Cordova, Angew. Chem. Int. Ed. 2005,44,1343; d) E. Reyes, A. Cordova, Tetrahedron Lett.2005,46,6605; c) A. Cordova, M. Engquist, I. Ibrahem, J. Casa, H. Sunden, Chem. Commun.2005, 2047.
19. D. Enders, C. Wang, J. W. Bats, Angew. Chem. Int. Ed.2008,47,7539.
20. T. Itoh, M. Yokoya, K. Miyauchi, K. Nagata, A. Ohsawa, Org. Lett.2003,5, 4301.
21. L.-Y. Wu, G. Bencivenni, M. Mancinelli, A. Mazzanti, G. Bartoli, P. Melchiorre, Angew. Chem. Int. Ed.2009,48,7196.
22. G. Bencivenni, L.-Y. Wu, A. Mazzanti, B. Giannichi, F. Pesciaioli, M.-P. Song, G. Bartoli, P. Melchiorre, Angew. Chem. Int. Ed.2009,48,7200.
23. For proline-catalyzed a-aminohydroxylation reactions, see:a) G. Zhong, Angew. Chem. Int. Ed.2003,42,4247; b) S. P. Brown, M. P. Brochu, C. J. Sinz, D.W. C. MacMillan, J. Am. Chem. Soc.2003,125,10808; c) Y. Hayashi, J. Yamaguchi, K. Hibino, M. Shoji, Tetrahedron Lett.2003,44,8293.
24. Y. Yamamoto, N. Momiyama, H. Yamamoto, J. Am. Chem. Soc.2004,126, 5962.
25. H. Sunden, I. Ibrahem, L. Eriksen, A. Cordova, Angew. Chem. Int. Ed.2005,44, 4877.
26. H. Yang, R. G. Carter, J. Org. Chem.2009,74,5151.
27. D. Enders, M. R. M. Huttl, C. Grondal, G. Raabe, Nature 2006,441,861.
28. D. Enders, M. R. M. Huttl, J. Runsink, G. Raabe, B. Wendt, Angew. Chem. Int. Ed.2007,46,467.
29. A. Carlone, S. Cabrera, M. Marigo, K. A. Jφgensen, Angew. Chem. Int. Ed.2007, 46,1101.
30. D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Angew. Chem. Int. Ed.2003, 42,4233.
31. D. B. Ramachary, C. F. Barbas Ⅲ, Chem. Eur. J.2004,10,5323. For further extensions, see:D. B. Ramachary, K. Anebousely, N. S. Chowdary, C. F. Barbas Ⅲ, J. Org. Chem.2004,69,5838.
32. Y.-K. Liu, C. Ma, K. Jiang, T.-Y. Liu, Y.-C. Chen, Org. Lett.2009,11,2848.
33. M. Marigo, S.Bertelsen, A. Landa, K. A. Jφgensen, J. Am. Chem. Soc.2006,128, 5745.
34. Y. Hayashi, T. Okano, S. Aratake, D. Hazelard, Angew. Chem. Int. Ed.2007,46, 4922.
35. E. Reyes, H. Jiang, A. Milelli, P. Elsner, R. G. Hazell, K. A. Jogensen, Angew. Chem. Int. Ed.2007,46,9202.
36. W. Chen, W. Du, Y.-Z. Duan, Y. Wu, S.-Y. Yang, Y.-C. Chen, Angew. Chem. Int. Ed.2007,46,7667.
37. B. Han, J.-L. Li, C. Ma, S.-J. Zhang, Y.-C. Chen, Angew. Chem. Int. Ed.2008,47, 9971.
38. B. Han, Z.-Q. He, J.-L. Li, R. Li, K. Jiang, T.-Y. Liu, Y.-C. Chen, Angew. Chem. Int. Ed.2009,48,5474.
39. S. Cabrera, J. Aleman, P. Bolze, S. Bertelsen, K. A. Jφgensen, Angew. Chem. Int. Ed.2008,47,121.
40. a)Y. Huang, A. M. Walji, C. H. Larsen, D. W. C. MacMillan, J. Am. Chem. Soc. 2005,127,15051; b) B. Simmons, A. M.Walji, D. W. C.MacMillan, Angew. Chem., Int. Ed.2009,48,4349; c) Y. Wang, D.-F. Yu, Y.-Z. Liu, H. Wei, Y.-C. Luo, D. J. Dixon, P.-F. Xu, Chem. Eur. J.2010,16,3922.
41. S. P. Lathrop, T. Rovis, J. Am. Chem. Soc.2009,131,13628.
42. For reviews, see:a) P. R. Schreiner, Chem. Soc. Rev.2003,32,289; b) P. M. Pihko, Angew. Chem. Int. Ed.2004,43,2062; c) C. Bolm, T. Rantanen, I. Schiffers, L. Zani, Angew. Chem. Int. Ed.2005,44,1785; d) M. S. Taylor, E. N. Jacobsen, Angew. Chem. Int. Ed.2006,45,1520; e) S. J. Connon, Angew. Chem. Int. Ed.2006,45,3909; f) T. Akiyama, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2006,348,999.
43. a) Y. Hoashi, T. Yabuta, Y. Takemoto, Tetrahedron Lett.2004,45,9185; b)Y. Hoashi, T. Yabuta, P. Yuan, H. Miyabe, Y. Takemoto, Tetrahedron 2006,62, 365.
44. M. Rueping, C. Azap, Angew. Chem. Int. Ed.2006,45,7832.
45. J. Seayad, A. M. Seayad, B. List, J. Am. Chem. Soc.2006,128,1086.
46. J. Itoh, K. Fuchibe, T. Akiyama, Angew. Chem. Int. Ed.2006,45,4796.
47. M. Rueping A. P. Antonchick, Angew. Chem. Int. Ed.2008,47,5836.
48. J. Zhou, B. List, J. Am. Chem. Soc.2007,129,7498.
49. M. Rueping, A. P. Antonchick, E. Sugiono, K. Grenader, Angew. Chem. Int. Ed. 2009,48,908.
50. H. Liu, G. Dagousset, G. Masson, P. Retailleau, J. Zhu, J. Am. Chem. Soc.2009, 131,4598.
51. a) H. Finch, E. A. Peterson, S. A. Ballard, J. Am. Chem. Soc.1952,74,2016; b) R. F. Evans, Aust. J. Chem.1967,20,1643; c) C. Jutz, A. F. Kirschner, R.-M. Wagner, Chem. Ber.1977,110,1259; d) I. A. Perillo, M. B. Garcia, J. A. Bisceglia, L. R. Orelli, J. Heterocycl. Chem.2002,39,655; e) A. R. Katrizky, S. K. Singh, H.-Y. He, J. Org. Chem.2002,67,3115.
52. a) M. Mayr, M. R.Buchmeiser, Macomol. Rapid Commun.2004,25,231; b) M. Mayr, K.Wurst, K.-H.Ongania, M. R.Buchmeiser, Chem. Eur. J.2004,10,1256.
53. a) I. Ibrahem, J. Casas, A. Cordova, Angew. Chem., Int. Ed.2004,43,6528; b) I. Ibrahem, W. Zou, J. Casas, H. Sunden, A. Cordova, Tetrahedron 2006,62,357.
1. a) A. Jossang, P. Jossang,H. A. Hadi, T. Sevenet, B. Bodo, J. Org. Chem.1991, 56,6527; b) R. Thericke, Y. Q. Tang, I. Sattler, S. Grabley, X. Z. Feng, Eur. J. Org. Chem.2001,261; c) C. Marti, E. M. Carreira, Eur. J. Org. Chem.2003, 2209; d) M. Tsuda, T. Mugishima, K. Komatzu, T. Sone, M. Tanaka, Y. Mikaimi, M. Shiro, M. Hirai, Y. Ohizumii, J. Kobayashi, Tetrahedron Lett.2003,59,3227; e) C. V. Galliford, K. A. Scheidt, Angew. Chem. Int. Ed.2007,46,8748; f) J. S. Bindra, in:The Alkaloids (Ed.:R. H. F. Manske), Academic Press, New York, 1973, vol.14, pp.84-121. g) X. Zhang, C. D. Smith, Mol. Pharmacol.1996,49, 288.
2. R. J. Sundberg, Indoles, Academic Press, London,1996, pp.17,152-154.
3. a) A. H. Beckett, R. W. Daisley, J. Walker, Tetrahedron 1968,24,6093, and references therein; b) D. Ben-Ishai, N. Peled, I. Sataty, Tetrahedron Lett.1980, 21,569.
4. a) R. M. Acheson, J. M. Vernon and R. W. Snaith, J. Chem. Soc.,1964,3229; b) J. M. Muchowski, Can. J. Chem.,1970,48,422; c) A.Walser, J. F. Blount and R. I. Fryer, J. Org. Chem.,1973,38,3077.
5. a) N. Finch and W. I. Taylor, J. Am. Chem. Soc.,1962,84,3871; b) K. V. Lichman, J. Chem. Soc. C,1971,2539.
6. M. Ito, C. W. Clark, M. Mortimore, J. B. Goh and S. F. Martin, J. Am. Chem. Soc.,2001,123,8003.
7. A. Bischler, B. Napiralsky, Ber. Dtsch. Chem. Ges.1893,26,1903.
8. a) N. Finch, W. I. Taylor, J. Am. Chem. Soc.1962,84,1318; b) N. Finch, W. I. Taylor, J. Am. Chem. Soc.1962,84,3871.
9. a) S. F. Martin, M. Mortimore, Tetrahedron Lett.1990,31,4557; b) S. F. Martin, B.; Benage, L. S. Geraci, J. E. Hunter, M. Mortimore, J. Am. Chem. Soc.1991, 113,6161.
10. A. Deiters, M. Petterson, S. F. Martin, J. Org. Chem.,2006,71,6547.
11. a) C. Pellegrini, C. Strassler, M. Weber, H. J. Borschberg, Tetrahedron: Asymmetry 1994,5,1979; b) C. Pellegrini, M. Weber, H. J. Borschberg, Helv. Chim. Acta 1996,79,151.
12. a) S. D. Edmondson, S. J. Danishefsky, Angew. Chem. Int. Ed.1998,37,1138;b) S. D. Edmondson, S. J. Danishefsky, L. Sepp-Lorenzino, N. Rosen, J. Am. Chem. Soc.1999,121,2147.
13. H. S. Wang, A. Ganesan, J. Org. Chem.2000,65,4685.
14. M. Somei, K. Noguchi, R. Yamagami, Y. Kawada, K. Yamada, F. Yamada, Heterocycles 2000,53,7.
15. N. Finch, I. H. C. Hsu, C. W. Gemenden, W. I. Taylor, J. Am.Chem. Soc.1963, 85,1520.
16. A. Jossang, P. Jossang, H. A. Hadi, T. Sevenet, B. Bodo, J.Org. Chem.1991,56, 6527.
17. a) A. C. Peterson, J. M. Cook, Tetrahedron Lett.1994,35,2651; b) A. C. Peterson, J. M. Cook, J. Org. Chem.1995,60,120.
18. a) P. Yu, J. M. Cook, J. Org. Chem.1998,63,9160; b) P. Yu, T. Wang, J. Li, J. M. Cook, J. Org. Chem.2000,65,3173; c) X. Z. Wearing, J. M. Cook, Org. Lett. 2002,4,4237.
19. M. Lachia, C. Poriel, A. Z. Slawin, Christopher J. Moody, Chem. Commun.2007, 286.
20. I. D. Hills, G. C. Fu, Angew. Chem. Int. Ed.2003,42,3921.
21. T. Sawada, D. E. Fuerst, J. L. Wood, Tetrahedron Lett.2003,44,4919.
22. B. M. Trost, M. K. Brennan, Org. Lett.2006,8,2027.
23. H. Miyamoto, Y. Okawa, A. Nakazaki, S. Kobayashi, Angew. Chem. Int. Ed. 2006,45,2274.
24. H. Miyamoto, Y. Okawa, A. Nakazaki, S. Kobayashi, Tetrahedron Lett.2007,48, 1805.
25. a) J.-F. Carpentier, A. Morteux, Tetrahedron: Asymmetry 1997,8,1083; b) K. Funabashi, M. Jachmann, M. Kanai, M. Shibasaki, Angew. Chem. Int. Ed.2003, 42,5489; c) G. Luppi, P. G. Cozzi, M. Monari, B. Kaptein, Q. B. Broxterman, C. Tomasini, J. Org. Chem.2005,70,7418; d) G. Chen, Y. Wang, H. He, S. Gao, X. Yang, X. Hao, Heterocycles 2006,68,2327; e) G. Luppi, M. Monari, R. J. Correa, F. A. Violante, A. C. Pinto, B. Kaptein, Q. B. Broxterman, S. J. Garden, C. Tomasini, Tetrahedron 2006,62,12017; f) M. Kitajima, I. Mori, K. Arai, N. Kogure, H.mTakayama, Tetrahedron Lett.2006,47,3199; g) B Alcaide, P. Almendros, R. Rodriguez-Acebes, J. Org. Chem.2006,71,2346; h) A. V. Malkov, M. A. Kabeshov, M. Bella, O. Kysilka, D. A. Malyshev, K. Pluhackova, P. Kocovsky, Org. Lett.2007,9,5473; i) J.-R. Chen, X.-P. Liu, X.-Y. Zhu, L. Liang, Y.-F. Qiao, J.-M. Zhang, W.-J. Xiao, Tetrahedron 2007,63,10437; j) R. J. Correa, S. J. Garden, G. Angelici, C. Tomasini, Eur. J. Org. Chem.2008,736; k) S. Nakamura, N. Hara, H. Nakashima, K. Kubo, N. Shibata, T. Toru, Chem. Eur. J. 2008,14,8079; 1) H. Lai, Z. Huang, Q. Wu, Y. Qin, J. Org. Chem.2009,74, 283.
26. K. C. Nicolaou, P. B. Rao, J. Hao, M. V. Reddy,G. Rassias, X. Huang, D. Y.-K. Chen, S. A. Snyder, Angew. Chem. Int. Ed.2003,42,1753.
27. R. Shintani, M. Inoue, T. Hayashi, Angew. Chem. Int. Ed.2006,45,3353.
28. P. Y. Toullec, R. B. C. Jagt, J. G. De Vries, B. L. Feringa, A. J. Minnaard, Org. Lett.2006,8,2715.
29. J. Itoh, S. B. Han, M. J. Krische, Angew. Chem. Int. Ed.2009,48,6313.
30. a) I. S. Kim, M.-Y. Ngai, M. J. Krische, J. Am. Chem. Soc.2008,130,14891; b) I. S. Kim, S. B. Han, M. J. Krische, J. Am. Chem. Soc.2009,131,2514.
31. N. V. Hanhan, A. H. Sahin, T. W. Chang, J. C. Fettinger, A. K. Franz, Angew. Chem. Int. Ed.2010,49,744.
32. V. Nair, S. Vellalath, M. Poonoth, R. Mohan, E. Suresh, Org. Lett.2006,8,507.
33. D. Basavaiah, K, R, Reddy, Org. Lett.2007,9,57.
34. V. Schulz, M. Davoust, M. Lemarie, J-F Lohier, J. S. de Santos, P. Metzner, J-F. Briere, Org. Lett.2007,9,1745.
35. D. Basavaiah, J. S. Rao, R. J. Reddy, A. J. Rao, Chem. Commun.,2005,2621.
36. K. Jones, J. Wilkinson,J. Chem. Soc., Chem. Commun.1992,1767.
37. J. Cossy, M. Cases, D. G.Pardo, Tetrahedron Lett.1998,39,2331.
38. S. T. Hilton, T. C. T. Ho, G. Pljevaljcic, K. Jones, Org. Lett.2000,2,2639.
39. a) C. Escolano,K. Jones, Tetrahedron Lett.2000,41,8951; b) C. Escolano, K. Jones, Tetrahedron 2002,58,1453.
40. D. Lizos, R. Tripoli, J. A. Murphy, Chem. Commun.2001,2732.
41. a) M. M. Abelman, T. Oh, L. E. Overman, J. Org. Chem.1987,52,4130; b) A. Ashimori, L. E. Overman, J. Org. Chem.1992,57,4571; c) A. Ashimori, B. Bachand, L. E. Overman, D. J. Poon, J. Am. Chem. Soc.1998,120,6477; d) A. Ashimori, B. Bachand, M. A. Calter, S. P. Govek, L. E. Overman, D. J. Poon, J. Am. Chem. Soc.1998,120,6488.
42. a) W. G. Earley, T. Oh, L. E. Overman, Tetrahedron Lett.1988,29,3785; b) A. Madin, C. J. O'Donnell, T. Oh, D. W. Old, L. E. Overman, M. J. Sharp, Angew. Chem. Int. Ed.1999,38,2934; c) W. G. B. Beyersbergen van Henegouwen, R. M. Fieseler, F. Rutjes, H. Hiemstra, Angew. Chem. Int. Ed.1999,38,2214; d) W. G. B. Beyersbergen van Henegouwen, R. M. Fieseler, F. Rutjes, H. Hiemstra, J. Org. Chem.2000,65,8317.
43. a) A. B. Dounay, K. Hatanaka, J. J. Kodanko, M. Oestreich, L. E. Overman, L. A. Pfeifer, M. M. Weiss, J. Am. Chem. Soc.2003,125,6261; b) A. Huang, J. J. Kodanko, L. E. Overman, J. Am. Chem. Soc.2004,126,14043.
44. L. E. Overman, M. D. Rosen, Angew. Chem. Int. Ed.2000,39,4596.
45. P. Liu, J. H. Seo, S. M. Weinreb, Angew. Chem. Int. Ed.2010,49,2000.
46. R. T. Ruck, M. A. Huffman, M. M. Kim, M. Shevlin, W. V. Kandur, Ian W. Davies, Angew. Chem. Int. Ed.2008,47,4711.
47. A. Pinto, Y. Jia, L. Neuville, J. Zhu, Chem. Eur. J.2007,13,961.
48. a) K. H. Shaughnessy, B. C. Hamann, J. F. Hartwig, J. Org. Chem.1998,63, 6546; b) S. Lee, J. F. Hartwig, J. Org. Chem.2001,66,3402.
49. a) R. Freund, W. W. K. R. Mederski, Helv. Chim. Acta.2000,83,1247; b) T. Y. Zhang, H. Zhang, Tetrahedron Lett.2002,43,193; c) T. Y.; Zhang, H. Zhang, Tetrahedron Lett.2002,43,1363; d) G. C. Bignan, K. Battista, P. J. Connolly, M. J. Orsini, J. Liu, S. A. Middleton, B. A. Reitz, Bioorg. Med. Chem. Lett.2005,15, 5022; e) S. P. Marsden, E. L.Watson, S. A. Raw, Org. Lett.2008,10,2905; f) J. M. Hillgren, S. P. Marsden, J. Org. Chem.2008,73,6459; g) L. Ackermann, R. Vicente, N. Hofmann, Org. Lett.2009,11, 4274.
50. a) F. Glorius, G. Altenhoff, R. Goddard, C. Lehmann, Chem. Commun.2002, 2704; b) T. Arao, K. Kondo, T. Aoyama, Tetrahedron Lett.2006,47,1417; c) E. P. Kundig, T. M. Seidel, Y.-X. Jia, G. Bernardinelli, Angew. Chem. Int. Ed.2007, 46,8484; d) Y.-X. Jia, J. M. Hillgren, E. L. Watson, S. P. Marsden, E. P. Kundig, Chem. Commun.2008,4040.
51. W. Erb, L. Neuville, J. Zhu, J. Org. Chem.2009,74,3109.
52. E. J. Hennessy, S. L. Buchwald, J. Am. Chem. Soc.2003,125,12084.
53. Y.-X. Jia, E. P. Kundig, Angew. Chem. Int. Ed.2009,48,1636.
54. A. Perry, R. J. K. Taylor, Chem. Commun.,2009,3249.
55. L. A. McAllister, S. Brand, R. de Gentile, D. J. Procter, Chem. Commun.,2003, 2380.
56. a) L. A. McAllister, R. A. McCormick, S. Brand, D. J. Procter, Angew. Chem. Int. Ed.2005,44,452; b) M. Miller, W. Tsang, A. Merritt, D. J. Procter, Chem. Commun.,2007,498.
57. W. S. Cheung, R. J. Patch, M. R. Player, J. Org. Chem.2005,70,3741.
58. R. Yanada, S. Obika, T. Inokuma, K. Yanada, M. Yamashita, S. Ohta, Y. Takemoto, J. Org. Chem.2005,70,6972.
59. R. Yanada, S. Obika, M. Oyama, Y. Takemoto, Org. Lett.2004,6,2825.
60. R. Shintani, T. Yamagami, T. Hayashi, Org. Lett.2006,8,4799.
61. D. M. D’Souza, F. Rominger, T. J. J. Muller, Angew. Chem. Int. Ed.2005,44, 153.
62. T.-S. Jiang, R.-Y. Tang, X.-G. Zhang, X.-H. Li, J.-H. Li, J. Org. Chem.2009,74, 8834.
63. a) A. Pinto, L. Neuville, P. Retailleu, J. Zhu, Org. Lett.2006,8,4927; b) A. Pinto, L. Neuville, J. Zhu, Angew. Chem. Int. Ed.2007,46,3291.
64. a) S.Tang, P. Peng, S.-F. Pi, Y. Liang, N.-X. Wang, J.-H. Li, Org. Lett.2008,10, 1179; b) S.Tang, P. Peng, Z.-Q. Wang, B.-X. Tang, C.-L. Deng, J.-H. Li, P. Zhong, N.-X. Wang, Org. Lett.2008,10,1875.
65. S. Kamijo, Y. Sasaki, C. Kanazawa, T. Schuβler, Y. Yamamoto, Angew. Chem. Int. Ed.2005,44,7718.
66. T. Miura, T. Toyoshima, Y. Takahashi, M. Murakami, Org. Lett.2009,11,2141.
67. T. Miura, Y. Takahashi, M. Murakami, Org. Lett.2007,9,5075.
68. S. Jaegli, J.-P. Vors, L. Neuville, J. Zhu, Synlett 2009,2997.
69. S. Jaegli, W. Erb, P. Retailleau, J.-P. Vors, L. Neuville, J. Zhu, Chem. Eur. J. 2010,16,5863.