基于芳基乙酮的芳基-α-酮酸酯的高效一锅法合成及其在不对称氢化中的应用探索
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摘要
芳基-α-酮酸酯在生物代谢过程中扮演了重要的角色。他们在一些天然产物中作为物质骨架。除此之外,芳基-α-酮酸酯还被用来作为合成生物活性体的重要中间物,芳基-α-酮酸酯同时还表现出一定的防晒功效。
在过去的几十年,曾出现过很多关于芳基-α-酮酸酯的合成方法,然而分析所有的这些方法,发现它们反应条件苛刻、反应步骤复杂、同时伴随着产率较低。这些缺点及不足都限制了芳基-α-酮酸酯在合成领域的发展应用。在此论文中,我们报道了一种未经报道的、全新的,由简单易得的原料芳基乙酮出发,采用一锅法制备芳基-α-酮酸酯的高效合成方法。
光学纯芳基-α-羟基酸及其衍生物在有机合成中是非常有用的原料和活性中间体。例如(R)-α-羟基-4-苯基丁酸乙酯就是普利类药物的重要中间体,但到目前为止,其主要来源于拆分,利用不对称氢化获得的成功例子很少。而在所有的制备光学纯的α-羟基酸及其衍生物方法中,最为有效的是通过不对称催化氢化相应的α-酮酸酯来制备。本论文尝试了一系列新概念手性配体来催化芳基-α-酮酸酯以获得相应的手性芳基-α-羟基酸酯。
α-Keto esters play an essential role in biological processes. They serve as the backbones in some natural products. In addition, arylα-keto esters are also used as key intermediates for the synthesis of bioactive compounds.α-Keto esters also show antisunburn effects.
In the past several decades, there was much attention fixed on the synthesis ofα-keto esters. However all these methods involved either strict conditions, or complicated procedures, or in some cases the low yield and all of these drawbacks extremely limited its application. Herein we report a convenient route to synthesizeα-keto esters from aryl-ketones via the one-pot method.
Optically pure aryl-α-hydroxyl acid and its derivatives are very important compounds or active intermediates. e.g., (R)-α-hydroxyl-4-phenyl ethyl butyrate is a kind of important intermediate of ACEI (Angiotensin-converting Enzyme Inhibitor). However they are almost obtained from chiral resolution by now. Asymmetric hydrogenation for preparing the optically pure aryl-α-hydroxyl acid and its derivatives is found to be an efficient method, but there is few successful case. Herein we reported a series of new concept chiral ligands to catalyzeα-keto ester to obtain corresponding chiral aryl-α-hydroxyl ester.
在过去的几十年,曾出现过很多关于芳基-α-酮酸酯的合成方法,然而分析所有的这些方法,发现它们反应条件苛刻、反应步骤复杂、同时伴随着产率较低。这些缺点及不足都限制了芳基-α-酮酸酯在合成领域的发展应用。在此论文中,我们报道了一种未经报道的、全新的,由简单易得的原料芳基乙酮出发,采用一锅法制备芳基-α-酮酸酯的高效合成方法。
光学纯芳基-α-羟基酸及其衍生物在有机合成中是非常有用的原料和活性中间体。例如(R)-α-羟基-4-苯基丁酸乙酯就是普利类药物的重要中间体,但到目前为止,其主要来源于拆分,利用不对称氢化获得的成功例子很少。而在所有的制备光学纯的α-羟基酸及其衍生物方法中,最为有效的是通过不对称催化氢化相应的α-酮酸酯来制备。本论文尝试了一系列新概念手性配体来催化芳基-α-酮酸酯以获得相应的手性芳基-α-羟基酸酯。
α-Keto esters play an essential role in biological processes. They serve as the backbones in some natural products. In addition, arylα-keto esters are also used as key intermediates for the synthesis of bioactive compounds.α-Keto esters also show antisunburn effects.
In the past several decades, there was much attention fixed on the synthesis ofα-keto esters. However all these methods involved either strict conditions, or complicated procedures, or in some cases the low yield and all of these drawbacks extremely limited its application. Herein we report a convenient route to synthesizeα-keto esters from aryl-ketones via the one-pot method.
Optically pure aryl-α-hydroxyl acid and its derivatives are very important compounds or active intermediates. e.g., (R)-α-hydroxyl-4-phenyl ethyl butyrate is a kind of important intermediate of ACEI (Angiotensin-converting Enzyme Inhibitor). However they are almost obtained from chiral resolution by now. Asymmetric hydrogenation for preparing the optically pure aryl-α-hydroxyl acid and its derivatives is found to be an efficient method, but there is few successful case. Herein we reported a series of new concept chiral ligands to catalyzeα-keto ester to obtain corresponding chiral aryl-α-hydroxyl ester.
引文
[1].戴立信,陆熙炎,朱光美.化学通报, 1995, 6, 15-22.
[2]. J. Seyden-Penne. John Wiley & Sons. New York, 1995.
[3].林国强,陈耀全,陈新滋,李月明.科学出版社, 2000, 1-5.
[4]. (a) Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127-2129. (b) Evans, D. A.; Hu, E.; Burch, J. D.; Jaeschke, G. J. Am. Chem. Soc. 2002, 124, 5654-5655.
[5]. (a) Oppolzer, W.; Moretti, R.; Thomi, S. Tetrahedron Lett. 1989, 30, 5603-5606. (b) Davis, F. A.; Towson, J. C.; Weismiller, M. C.; Lal, S.; Carroll, P. J. J. Am. Chem. Soc. 1988, 110, 8477-8482.
[6]. Nozaki, H.; Moriuti, S.; Takaya, H.; Noyiri, R. Tetrahedron Lett. 1966, 7, 5239-5244.
[7]. (a) Noyori, R. Wiley: New York, 1994. (b) Ojima, I. Ed. VCH Publisher: New York, 1993.
[8]. Negent, W. A.; Rajanbabn, T. V.; Burk, M. J. Science, 1993, 259, 479-483.
[9]. (a) Knowles, W. S. Acc. Chem. Res. 1983, 16, 106-112. (b) Vineyard, B. D.;Knowles, W. S.; Sabacky, W. J.; Bachman, G. L.; Weinkautt, D. J. J. Am. Chem. Soc. 1977, 99, 5946-5952.
[10]. Noyori, R. Adv. Synth. Catal. 2003, 345, 15.
[11]. Calvin, M. J. Am. Chem. Soc. 1939, 61, 2230-2234.
[12]. Nakamura, Y. Bull. Chem. Soc. Jpn. 1941, 16, 367-370.
[13]. Akabori, S.; Sakurai, S.; Izumi, Y.; Fujii, Y. Nature. 1956, 178, 323-324.
[14]. Halpern, J.; Harrod, J. F.; James, B. R. J. Am. Chem. Soc. 1961, 83, 753-754.
[15]. Young, J. F.; Osborn, J. A.; Jardine, F. H.; Wilkinson, G. Chem. Commun. 1965, 131-132.
[16]. (a) Knowles, W. S.; Sabacky, M. J. Chem. Commun. 1968, 1445-1446; (b) Knowles, W. S. Angew. Chem. Int. Ed. 2002, 41, 1998-2007.
[17]. Horner, L.; Siegel, H.; Buthe, H. Angew. Chem. Int. Ed. 1968, 7, 942.
[18]. Dang, T. P.; Kagan, H. B. J. Chem. Soc. Chem. Commun. 1971, 481.
[19]. (a) Knowles, W. S.; Sabacky, M. J.; Vineyard, B. D. J. Chem. Soc. Chem. Commun. 1972, 10; (b) Vineyard, B. D.; Knowles, W. S.; Sabacky, M. J.; Bachman, G. L.; Weinkauff, D. J. J. Am. Chem. Soc. 1977, 99, 5946-5952; (c) Knowles, W. S. Acc. Chem. Res. 1983, 16, 106-112.
[20]. Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932-7934.
[21]. (a) Halpern, J. Acc. Chem. Res. 1982, 15, 332-338; (b) Halpern, J. Pure Appl. Chem. 1983, 55, 99-106; (c) Landis, C. R.; Halpern, J. J. Am. Chem. Soc. 1987, 109, 1746-1754.
[22]. Brown, J. M. in Comprehensive Asymmetric Catalysis, Eds: Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H.; Springer, Berlin, 1999, 1, 124-127; (b) Giernoth, R.; Heinrich, H.; Adams, N. J.; Deeth, R. J.; Bargon, J.; Brown, J. M. PHIP J. Am. Chem. Soc. 2000, 122, 12381-12382.
[23]. (a) Burk, M. J.; Feaster, J. E.; Harlow, R. L. Organometallics 1990, 9, 2653-2655; (b) Burk, M. J.; Harlow, R. L. Angew. Chem. Int. Ed. 1990, 29, 1462-1464.
[24]. (a) Ojima, I. Ed. Catalytic Asymmetric Synthesis VCH Publishers; New York, 1999. (b) Noyori, R. Ed. Organic Synthesis; Wiley; New York, 1994. (c) Jacobensen, E. N., Pfaltz, A.; Yamamoto, H. Eds. Berlin, 1999, Vol.1.
[25].陈新滋.中国高校科技与产业化2002, 16-19
[26]. Blaser, H.-U.; Spindler, F.; Studer, M. Applied Catalysis A: General 2001, 221, 119.
[27]. (a) Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, Germany, 1999; Vols. I-III. (b) Catalysis Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000. (c) Coppola, G. M.; Schuster, H. F.α-Hydroxy Acids in Enantioselective Synthesis; VCH: Weinhein, Germany, 1997.
[28]. (a) Wilen, S. H. Tables of Resolving Agents and Optical Resolutions, Eliel, E. L. Ed.; University of Notre Dame: Notre Dame, 1972. (b) Newman, P. OpticalResolution Procedures for Chemical Compouds, Riverdale, New York, 1978. (c) Mashraqui, S. H.; Kellogg, R. M.; J. Org. Chem. 1984, 49, 2513. (d) Corey, E, J.; Naef, R.; Hannon, F. J. J. Am. Chem. Soc. 1986, 108, 7114. (e) Blay, G.; Fernandez, I.; Monje, B.; Pedro, J. R. Tetrahedron Lett. 2004, 45, 8039. (f) Lesac, A.; Narancic, S.; Sepelj, M.; Bruce, D. W.; Sunjic, V. Tetrahedron: Asymmetry 2003,45,2731.
[29]. (a) Ono, S.; Yamafuji, T.; Chaki, H. Chem. Pharm. Bull. 1995, 43, 1492. (b) Defreyn, G.; Gachet, C.; Savi, P.; Driot, F.; Cazenave, J.; Maffrand, J. P. Thromb. Haemostasis 1991, 65, 186. (c) Griffiths, R. G.; Dancer, J.; O’Neill, E.; Harwood, J. L. New Phytologist 2003, 158, 345.
[30]. (a) Ohnishi, Y.; Kagarni, M.; Ohno, A. J. Am. Chem. Soc. 1975, 97, 4766. (b) Ohno, A.; Ikeguchi, M.; Kimura, T.; Oka, S. J. Am. Chem. Soc. 1979, 101, 7036. (c) de Vries, J. G.; Kellogg, R. M. J. Am. Chem. Soc. 1979, 101, 2759. (d) Seki, M.; Baba, N.; Oda, J.; Inouye, Y. J. Am. Chem. Soc. 1981, 103, 4613. (e) Meyers, A. I.; Brown, J. D. J. Am. Chem. Soc. 1987, 109, 3155. (f) Kanomata, N.; Nakata, T. Angew. Chem., Int. Ed. 1997, 36, 1207. (g) Adam, W.; Lazarus, M.; Boss, B.; Saha-M?ller, C. R.; Humpf, H.-U.; Schreier, P. J. Org. Chem. 1997, 62, 7841. (h) Kanomata, N.; Nakata, T. J. Am. Chem. Soc. 2000, 122, 4563. (i) Zhu, D.; Yang, Y.; Hua, L. J. Org. Chem. 2006, 71, 4202. (j) Landwehr, M.; Hochrein, L.; Otey, C. R.; Kasrayan, A.; Backvall, J.-E.; Arnold, F. H. J. Am. Chem. Soc. 2006. 128, 6058. (h) Ema, T.; Okita, N.; Ide, S.; Sakai, T. Org. Biomol. Chem. 2007, 5, 1175. (i) Kratzer, R.; Nidetzky, B. Chem. Commun. 2007, 1047.
[31]. (a) Brown, H. C.; Pai, G. G. J. Org. Chem. 1985, 50, 1384. (b) Singh, V. K. Synthesis 1992, 605. (c) Wang, Z.; La, B.; Fortunak, J. M.; Meng, X.-J.; Kabalka, G. W. Tetrahedron Lett. 1998, 39, 5501. (d) Ramachandran, P. V.; Pitre, S.; Brown, H. C. J. Org. Chem. 2002, 67, 5315.
[32]. (a) Solodin, I.; Goldberg, Y.; Zel?ans, G.; Lukevics, E. J. Chem. Soc., Chem. Commun. 1990, 1321. (b) Xiang, Y. B.; Snow, K.; Belley, M. J. Org. Chem. 1993, 58, 993. (c) Maitra, U.; Mathivanan, P. Tetrahedron: Asymmetry 1994, 5, 1171.
[33]. (a) Tang, L.; Deng, L. J. Am. Chem. Soc. 2002, 124, 2870. (b) Radosevich, A. T.; Musich, C.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 1090.
[34]. (a) Hamashima, Y.; Sawada, D.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 2641. (b) Sawada, D.; Shibasaki, M. Angew. Chem., Int. Ed. 2000, 39, 209. (c) Kanai, M.; Hamashima, Y.; Shibasaki, M. Tetrahedron Lett. 2000, 41, 2405. (d) Hamashima, Y.; Kanai, M.; Shibasaki, M.; J. Am. Chem. Soc. 2000, 122, 7412. (e) Hamashima, Y.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2001, 42, 691. (f) Tanaka, K.; Mori, A.; Inoue, S. J. Org. Chem. 1990, 55, 181. (g) Mori, A.; Nitta, H.; Kudo, M.; Inoue, S. Tetrahedron Lett. 1991, 32, 4333.
[35]. (a) Ojima, I.; Kogure, T.; Achiwa, K. J. Chem. Soc., Chem. Commun. 1977, 428. (b) Gamez, P.; Fache, F.; Mangeney, P.; Lemaire, M. Tetrahedron Lett. 1993, 34, 6897. (c) Gamez, P.; Fache, F.; Lemaire, M. Tetrahedron: Asymmetry 1995, 6, 705. (d) Blaser, H.-U.; Jalett, H.-P.; Spindler, F. J. Mol. Catal. A: Chem. 1996, 107, 85. (e) Cederbaum, F.; Lamberth, C.; Malan, C.; Naud, F.; Spindler, F.; Studer, M.; Blaser, H.-U. Adv. Synth. Catal. 2004, 346, 842. (f) Yang, J. W.; List, B. 2006, Org. Lett. 8, 5653.
[36]. (a) Baiker, A. J. Mol. Catal. A: Chem. 1997, 115, 473. (b) Blaser, H.-U.; Jalett, H. P.; Müller, M.; Studer, M. Catal. Today 1997, 37, 441. (c) Zuo, X.; Liu, H.; Guo, D.; Yang, X. Tetrahedron 1999, 55, 7787. (d) Studer, M.; Blaser, H.-U.; Exner, C. Adv. Synth. Catal. 2003, 345, 45. (e) Xing, L.; Du.; F, Liang.; J.-J.; Chen, Y.-S.; Zhou. Q.-L. J. Mol. Catal. A: Chem. 2007, 276, 191. (f) Mallat, T.; Orglmeister, E.; Baiker, A. Chem. Rev. 2007, 107, 4863.
[37]. Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071.
[38]. (a) Mashima, K.; Kusano, K.-h.; Sato, N.; Matsumura, Y.-i.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. (b) Carpentier, J.-F.; Mortreux, A. Tetrahedron: Asymmetry 1997, 8, 1083. (c) Pasquier, C.; Eilers, J.; Reiners, I.; Martens, J.; Mortreux, A.; Agbossou, F. Synlett 1998, 1162. (d) ter Halle, R.; Schultz, E.; Spagnol, M.; Lemaire, M. Synlett 2000, 680. (e) Tang, W.; Zhang, X .Chem. Rev.2003, 103, 3029 and references cited therein. (f) Jones, M. D.; Raja, R.; Thomas, J. M.; Johnson, B. F. G.; Lewis, D. W.; Rouzaud, J.; Harris, K. D. M. Angew. Chem., Int. Ed. 2003, 42, 4326. (g) Jeulin, S.; Duprat de Paule, S.; Ratovelomanana-Vidal, V.; Genet, J. P.; Champion, N.; Dellis, P. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5799. (h) Qiu, L.; Wu, J.; Chan, S.; Au-Yeung, T. T.-L.; Ji, J.-X.; Guo, R.; Pai, C.-C.; Zhou, Z.; Li, X.; Fan, Q.-H.; Chan, A. S. C. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5815. (i) Qiu, L.; Kwong, F. Y.; Wu, J.; Lam, W. H.; Chan, S.; Yu, W.-Y.; Li, Y.-M.; Guo, R.; Zhou, Z.; Chan, A. S. C. J. Am. Chem. Soc. 2006, 128, 5955. (j) Boaz, N. W.; Mackenzie, E. B.; Debenham, S. D.; Large, S. E.; Ponasik, J. A. J. Org. Chem. 2005, 70, 1872. (k) Wang, C.-J.; Sun, X.; Zhang, X. Synlett 2006, 1169. (l) Sun, X.; Zhou, L.; Li, W.; Zhang, X. J. Org. Chem. 2008, 73, 1143.
[39]. Li, L.-S.; Wu, Y.-L. Tetrahedron Lett. 2002, 43, 2427-2430.
[40]. (a) Patel, D. V.; Rielly, G. K.; Ryono, D. E.; Free, C. A.; Smith, S. A.; Petrillo, Jr. E. W. J. Med. Chem. 1993, 36, 2431-2447; (b) Ocain, T.; Rich, D. H. J. Med. Chem. 1992, 35, 451-456; (c) Iwanowicz, E. J.; Lin, J.; Roberts, D. G. M.; Michel, I. M.; Seiler, S. M. Bioorg. Med. Chem. Lett. 1992, 2, 1607-1612; (d) Angelastro, M. R.; Mehdi, S.; Burkhart, J. P.; Peet, N. P.; Bey, P. J. Med. Chem. 1990, 33, 11-13.
[41]. (a) Yuan, W.; Wong, C.-H.; Haeggstroem, J. Z.; Wetterholm, A.; Samuelsson, B. J. Am. Chem. Soc. 1992, 114, 6552-6553; (b) Yuan, W.; Munoz, B.; Wong, C.-H.; Haeggstroem, J. Z.; Wetterholm, A.; Samuelsson, B. J. Med. Chem. 1993, 36, 211-220.
[42]. Photis, J. M. Tetrahedron Lett. 1980, 21, 3539-3540.
[43]. Valentine, D. Jr.; Scott, J. W. Synthesis 1978, 329-356.
[44]. Schulte, K.; Meinzinger, E. Ger. 949,521, 1956; Chem. Abstr. 1958, 52, 19024c.
[45]. (a) Yamada, K.; Kato, M.; Iyoda, M.; Hirata, Y. J. Chem. Soc., Chem. Commun. 1973, 499-500; (b) Burkhart, J. P.; Peet, N. P.; Bey, P. Tetrahedron Lett. 1988, 29, 3433-3436.
[46]. Micetich, R. G. Org. Prep. Proced. Int. 1970, 2, 249-252.
[47]. Wasserman, H. H.; Ho, W.-B. J. Org. Chem. 1994, 59, 4364-4366.
[48]. Singh, J.; Kissick, T. P.; Mueller, R. H. Org. Prep. Proced. Int. 1989, 21, 501-510.
[49]. Corey, E. J.; Erickson, B. W. J. Org. Chem. 1971, 36, 3553-3560.
[50]. Babudri, F.; Fiandanese, V.; Marchese, G.; Punzi, A. Tetrahedron 1996, 52, 13513-13520 and references cited therein.
[51].李裕林,李绍白.高等学校化学学报1983, 4(3): 389-391.
[52]. Singh J.,Thomas P. K., Richard H. M.. Org. Prep. Proced. Int. 1989, 21(4): 501-504
[53]. Ma Ming, Li, C.-K., Peng, L.-L., Xie Fang, Zhang Xiu and Wang J-B, Tetrahedron Lett. 2005, 46, 3927-3929.
[54]. (a) Stocks, M. J.; Harrison, R. P.; Teague, S. J. Tetrahedron Lett. 1995, 36, 6555-6558; (b) Pirrung, M. C.; Tepper, R. J. J. Org. Chem. 1995, 60, 2461-2465. (c) Chen, Y.-T.; Onaran, M. B.; Doss, C. J.; Seto, C. T. Bioorg. Med. Chem. Lett. 2001, 11, 1935-1938; (d) Beebe, X.; Nilius, A. M.; Merta, P. J.; Soni, N. B.; Bui M. H.; Wagner. R.; Beutel, B. A. Bioorg. Med. Chem. Lett. 2003, 13, 3133-3136.
[55]. (a) Hanessian, S. Total Synthesis of Natural Products: The Chiron Approach; Pergamon Press: New York, 1983. (b) Seuring, B.; Seebach, D. Helv. Chim. Acta 1977, 60, 1175. (c) Mori, K.; Takigawa, T.; Matsuo, T. Tetrahedron 1979, 35, 933.
[56]. (a) Orito, Y.; Imai, S.; Niwa, S. Nippon Kagaku Kaishi 1979, 1118. (b) Orito, Y.; Imai, S.; Niwa, S. Nippon Kagaku Kaishi 1980, 670. (c) Orito, Y.; Imai, S.; Niwa, S. Nippon Kagaku Kaishi 1982, 137. (d) Blaser, H.-U.; Jalett, H. P.; Wiehl, J. J. Mol. Catal. 1991, 68, 215. (e) Spindler, F.; Pittelkow, U.; Blaser, H.-U. Chirality 1991, 3, 370. (f) Blaser, H.-U.; Jalett, H. P.; Spindler, F. J. Mol. Catal. 1996, 107, 85. (g) Blaser, H.-U.; Müller, M. Stud. Surf. Sci. Catal. 1991, 59, 73. (h) Webb, G.; Wells, P. B. Catal. Today 1992, 12, 319. (i) Augustine, R. L.; Tanieylan, S. K.; Doyle, L. K. Tetrahedron: Asymmetry 1993, 4, 1803. (j) Wang, G.; Heinz, T.; Pfaltz, A.; Minder, B.; Mallat, T.; Baiker, A. J. Chem. Soc., Chem.Commun. 1994, 2047. (k) Minder, P.; Schurch, M.; Mallat, T.; Baiker, A.; Heinz, T.; Pfaltz, A. J. Catal. 1996, 160, 261.
[57]. (a) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029; and references cited therein. (b) Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. (c) Chiba, T.; Miyashita, A.; Nohira, H.; Takaya, H. Tetrahedron Lett. 1993, 34, 2351. (d) Genet, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Bischoff, L.; Cano De Andrade, M. C.; Darses, S.; Galopin, C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 675. (e) Benincori, T.; Brenna, E.; Sannicolo, F.; Trimarco, L.; Antognazza, P.; Cesarotti, E.; Demartin, F.; Pilati, T. J. Org. Chem. 1996, 61, 6244. (f) Benincori, T.; Cesarotti, E.; Piccolo, O.; Sannicolo, F. J. Org. Chem. 2000, 65, 2043.
[58]. (a) Zhang, W.; Adachi, Y.; Hirao, T.; Ikeda, I. Tetrahedron: Asymmetry 1996, 7, 451-460. (b) Zhang, W.; Hirao, T.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545-4548.
[59]. (a) Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1996, 37, 7995-7998. (b) Zhang, W.; Shimanuki, T.; Kida, T.; Nakatsuji, Y.; Ikeda, I. J. Org. Chem. 1999, 64, 6247-6251.
[60]. (a) Kang, J., Lee, J., Ahn, A., Choi, J. Tetrahedron Lett. 1998, 39, 5523-5526. (b) Kang, J., Lee, J., Kim, J., Kim, G., Chirality, 2000, 12, 378-382.
[61]. (a) Ogihara, T.; Nakamaru, M.; Higaki, J.; Kumahara, Y.; Hamano, Y.; Minamino, T.; Nakamura, N. Curr. Ther. Res. 1987, 41, 809. (b) Miyake, A.; Itoh, K.; Oka, Y. Chem. Pharm. Bull. 1986, 34, 2852.
[62]. Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7933.
[63]. (a) T. Saito. U.S. Patent 5,872,273, 1999; (b) T. Saito; T. Yokozawa; T. Ishizaki; T. Moroi; N. Sayo; T. Miura; H. Kumobayashi, Adv. Synth. Catal. 2001, 343, 264; (c) Z. Zhang; H. Qian; J. Longmire; X. Zhang, J. Org. Chem. 2000, 65, 6223; (d) S. Wu; W. Wang; W. Tang; M. Lin; X. Zhang, Org. Lett. 2002, 4, 4495;(e) C.-C. Pai; Y.-M. Li; Z.-Y. Zhou; A. S. C. Chan, Tetrahedron Lett. 2002, 43, 2789.
[64]. Zhang, Z.; Qian, H.; Longmire, J.; Zhang, X. J. Org. Chem. 2000, 65,6223-6226.
[65]. Ohwada, T.; Shudo, K. J. Org. Chem. 1989, 54, 5227-5237.
[66]. Cohen, M. J.; McNelis, E. J. Org. Chem. 1984, 49, 515-518.
[67]. Kolasa, T.; Miller, M. J. J. Org. Chem. 1987, 52, 4978-4884.
[68]. Hjelmencrantz, A.; Berg, U. J. Org. Chem. 2002, 67, 3585-3594.
[69]. Muller, A. J.; Nishiyama, K.; Griffin, G. W.; Ishikawa, K.; Gibson, D. M. J. Org. Chem. 1982, 47, 2342-2352.
[70]. Katritzky, A. R.; Wang, Z.; Wells, A. P.; Steel, P. J. Org. Prep. Proced. Int. 1995, 27, 457-462.
[71]. Fokas, D.; Patterson, J. E.; Slobodkin, G.; Baldino, C. M. Tetrahedron Lett. 2003, 44, 5137-5140.
[2]. J. Seyden-Penne. John Wiley & Sons. New York, 1995.
[3].林国强,陈耀全,陈新滋,李月明.科学出版社, 2000, 1-5.
[4]. (a) Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127-2129. (b) Evans, D. A.; Hu, E.; Burch, J. D.; Jaeschke, G. J. Am. Chem. Soc. 2002, 124, 5654-5655.
[5]. (a) Oppolzer, W.; Moretti, R.; Thomi, S. Tetrahedron Lett. 1989, 30, 5603-5606. (b) Davis, F. A.; Towson, J. C.; Weismiller, M. C.; Lal, S.; Carroll, P. J. J. Am. Chem. Soc. 1988, 110, 8477-8482.
[6]. Nozaki, H.; Moriuti, S.; Takaya, H.; Noyiri, R. Tetrahedron Lett. 1966, 7, 5239-5244.
[7]. (a) Noyori, R. Wiley: New York, 1994. (b) Ojima, I. Ed. VCH Publisher: New York, 1993.
[8]. Negent, W. A.; Rajanbabn, T. V.; Burk, M. J. Science, 1993, 259, 479-483.
[9]. (a) Knowles, W. S. Acc. Chem. Res. 1983, 16, 106-112. (b) Vineyard, B. D.;Knowles, W. S.; Sabacky, W. J.; Bachman, G. L.; Weinkautt, D. J. J. Am. Chem. Soc. 1977, 99, 5946-5952.
[10]. Noyori, R. Adv. Synth. Catal. 2003, 345, 15.
[11]. Calvin, M. J. Am. Chem. Soc. 1939, 61, 2230-2234.
[12]. Nakamura, Y. Bull. Chem. Soc. Jpn. 1941, 16, 367-370.
[13]. Akabori, S.; Sakurai, S.; Izumi, Y.; Fujii, Y. Nature. 1956, 178, 323-324.
[14]. Halpern, J.; Harrod, J. F.; James, B. R. J. Am. Chem. Soc. 1961, 83, 753-754.
[15]. Young, J. F.; Osborn, J. A.; Jardine, F. H.; Wilkinson, G. Chem. Commun. 1965, 131-132.
[16]. (a) Knowles, W. S.; Sabacky, M. J. Chem. Commun. 1968, 1445-1446; (b) Knowles, W. S. Angew. Chem. Int. Ed. 2002, 41, 1998-2007.
[17]. Horner, L.; Siegel, H.; Buthe, H. Angew. Chem. Int. Ed. 1968, 7, 942.
[18]. Dang, T. P.; Kagan, H. B. J. Chem. Soc. Chem. Commun. 1971, 481.
[19]. (a) Knowles, W. S.; Sabacky, M. J.; Vineyard, B. D. J. Chem. Soc. Chem. Commun. 1972, 10; (b) Vineyard, B. D.; Knowles, W. S.; Sabacky, M. J.; Bachman, G. L.; Weinkauff, D. J. J. Am. Chem. Soc. 1977, 99, 5946-5952; (c) Knowles, W. S. Acc. Chem. Res. 1983, 16, 106-112.
[20]. Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932-7934.
[21]. (a) Halpern, J. Acc. Chem. Res. 1982, 15, 332-338; (b) Halpern, J. Pure Appl. Chem. 1983, 55, 99-106; (c) Landis, C. R.; Halpern, J. J. Am. Chem. Soc. 1987, 109, 1746-1754.
[22]. Brown, J. M. in Comprehensive Asymmetric Catalysis, Eds: Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H.; Springer, Berlin, 1999, 1, 124-127; (b) Giernoth, R.; Heinrich, H.; Adams, N. J.; Deeth, R. J.; Bargon, J.; Brown, J. M. PHIP J. Am. Chem. Soc. 2000, 122, 12381-12382.
[23]. (a) Burk, M. J.; Feaster, J. E.; Harlow, R. L. Organometallics 1990, 9, 2653-2655; (b) Burk, M. J.; Harlow, R. L. Angew. Chem. Int. Ed. 1990, 29, 1462-1464.
[24]. (a) Ojima, I. Ed. Catalytic Asymmetric Synthesis VCH Publishers; New York, 1999. (b) Noyori, R. Ed. Organic Synthesis; Wiley; New York, 1994. (c) Jacobensen, E. N., Pfaltz, A.; Yamamoto, H. Eds. Berlin, 1999, Vol.1.
[25].陈新滋.中国高校科技与产业化2002, 16-19
[26]. Blaser, H.-U.; Spindler, F.; Studer, M. Applied Catalysis A: General 2001, 221, 119.
[27]. (a) Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, Germany, 1999; Vols. I-III. (b) Catalysis Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000. (c) Coppola, G. M.; Schuster, H. F.α-Hydroxy Acids in Enantioselective Synthesis; VCH: Weinhein, Germany, 1997.
[28]. (a) Wilen, S. H. Tables of Resolving Agents and Optical Resolutions, Eliel, E. L. Ed.; University of Notre Dame: Notre Dame, 1972. (b) Newman, P. OpticalResolution Procedures for Chemical Compouds, Riverdale, New York, 1978. (c) Mashraqui, S. H.; Kellogg, R. M.; J. Org. Chem. 1984, 49, 2513. (d) Corey, E, J.; Naef, R.; Hannon, F. J. J. Am. Chem. Soc. 1986, 108, 7114. (e) Blay, G.; Fernandez, I.; Monje, B.; Pedro, J. R. Tetrahedron Lett. 2004, 45, 8039. (f) Lesac, A.; Narancic, S.; Sepelj, M.; Bruce, D. W.; Sunjic, V. Tetrahedron: Asymmetry 2003,45,2731.
[29]. (a) Ono, S.; Yamafuji, T.; Chaki, H. Chem. Pharm. Bull. 1995, 43, 1492. (b) Defreyn, G.; Gachet, C.; Savi, P.; Driot, F.; Cazenave, J.; Maffrand, J. P. Thromb. Haemostasis 1991, 65, 186. (c) Griffiths, R. G.; Dancer, J.; O’Neill, E.; Harwood, J. L. New Phytologist 2003, 158, 345.
[30]. (a) Ohnishi, Y.; Kagarni, M.; Ohno, A. J. Am. Chem. Soc. 1975, 97, 4766. (b) Ohno, A.; Ikeguchi, M.; Kimura, T.; Oka, S. J. Am. Chem. Soc. 1979, 101, 7036. (c) de Vries, J. G.; Kellogg, R. M. J. Am. Chem. Soc. 1979, 101, 2759. (d) Seki, M.; Baba, N.; Oda, J.; Inouye, Y. J. Am. Chem. Soc. 1981, 103, 4613. (e) Meyers, A. I.; Brown, J. D. J. Am. Chem. Soc. 1987, 109, 3155. (f) Kanomata, N.; Nakata, T. Angew. Chem., Int. Ed. 1997, 36, 1207. (g) Adam, W.; Lazarus, M.; Boss, B.; Saha-M?ller, C. R.; Humpf, H.-U.; Schreier, P. J. Org. Chem. 1997, 62, 7841. (h) Kanomata, N.; Nakata, T. J. Am. Chem. Soc. 2000, 122, 4563. (i) Zhu, D.; Yang, Y.; Hua, L. J. Org. Chem. 2006, 71, 4202. (j) Landwehr, M.; Hochrein, L.; Otey, C. R.; Kasrayan, A.; Backvall, J.-E.; Arnold, F. H. J. Am. Chem. Soc. 2006. 128, 6058. (h) Ema, T.; Okita, N.; Ide, S.; Sakai, T. Org. Biomol. Chem. 2007, 5, 1175. (i) Kratzer, R.; Nidetzky, B. Chem. Commun. 2007, 1047.
[31]. (a) Brown, H. C.; Pai, G. G. J. Org. Chem. 1985, 50, 1384. (b) Singh, V. K. Synthesis 1992, 605. (c) Wang, Z.; La, B.; Fortunak, J. M.; Meng, X.-J.; Kabalka, G. W. Tetrahedron Lett. 1998, 39, 5501. (d) Ramachandran, P. V.; Pitre, S.; Brown, H. C. J. Org. Chem. 2002, 67, 5315.
[32]. (a) Solodin, I.; Goldberg, Y.; Zel?ans, G.; Lukevics, E. J. Chem. Soc., Chem. Commun. 1990, 1321. (b) Xiang, Y. B.; Snow, K.; Belley, M. J. Org. Chem. 1993, 58, 993. (c) Maitra, U.; Mathivanan, P. Tetrahedron: Asymmetry 1994, 5, 1171.
[33]. (a) Tang, L.; Deng, L. J. Am. Chem. Soc. 2002, 124, 2870. (b) Radosevich, A. T.; Musich, C.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 1090.
[34]. (a) Hamashima, Y.; Sawada, D.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 2641. (b) Sawada, D.; Shibasaki, M. Angew. Chem., Int. Ed. 2000, 39, 209. (c) Kanai, M.; Hamashima, Y.; Shibasaki, M. Tetrahedron Lett. 2000, 41, 2405. (d) Hamashima, Y.; Kanai, M.; Shibasaki, M.; J. Am. Chem. Soc. 2000, 122, 7412. (e) Hamashima, Y.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2001, 42, 691. (f) Tanaka, K.; Mori, A.; Inoue, S. J. Org. Chem. 1990, 55, 181. (g) Mori, A.; Nitta, H.; Kudo, M.; Inoue, S. Tetrahedron Lett. 1991, 32, 4333.
[35]. (a) Ojima, I.; Kogure, T.; Achiwa, K. J. Chem. Soc., Chem. Commun. 1977, 428. (b) Gamez, P.; Fache, F.; Mangeney, P.; Lemaire, M. Tetrahedron Lett. 1993, 34, 6897. (c) Gamez, P.; Fache, F.; Lemaire, M. Tetrahedron: Asymmetry 1995, 6, 705. (d) Blaser, H.-U.; Jalett, H.-P.; Spindler, F. J. Mol. Catal. A: Chem. 1996, 107, 85. (e) Cederbaum, F.; Lamberth, C.; Malan, C.; Naud, F.; Spindler, F.; Studer, M.; Blaser, H.-U. Adv. Synth. Catal. 2004, 346, 842. (f) Yang, J. W.; List, B. 2006, Org. Lett. 8, 5653.
[36]. (a) Baiker, A. J. Mol. Catal. A: Chem. 1997, 115, 473. (b) Blaser, H.-U.; Jalett, H. P.; Müller, M.; Studer, M. Catal. Today 1997, 37, 441. (c) Zuo, X.; Liu, H.; Guo, D.; Yang, X. Tetrahedron 1999, 55, 7787. (d) Studer, M.; Blaser, H.-U.; Exner, C. Adv. Synth. Catal. 2003, 345, 45. (e) Xing, L.; Du.; F, Liang.; J.-J.; Chen, Y.-S.; Zhou. Q.-L. J. Mol. Catal. A: Chem. 2007, 276, 191. (f) Mallat, T.; Orglmeister, E.; Baiker, A. Chem. Rev. 2007, 107, 4863.
[37]. Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071.
[38]. (a) Mashima, K.; Kusano, K.-h.; Sato, N.; Matsumura, Y.-i.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. (b) Carpentier, J.-F.; Mortreux, A. Tetrahedron: Asymmetry 1997, 8, 1083. (c) Pasquier, C.; Eilers, J.; Reiners, I.; Martens, J.; Mortreux, A.; Agbossou, F. Synlett 1998, 1162. (d) ter Halle, R.; Schultz, E.; Spagnol, M.; Lemaire, M. Synlett 2000, 680. (e) Tang, W.; Zhang, X .Chem. Rev.2003, 103, 3029 and references cited therein. (f) Jones, M. D.; Raja, R.; Thomas, J. M.; Johnson, B. F. G.; Lewis, D. W.; Rouzaud, J.; Harris, K. D. M. Angew. Chem., Int. Ed. 2003, 42, 4326. (g) Jeulin, S.; Duprat de Paule, S.; Ratovelomanana-Vidal, V.; Genet, J. P.; Champion, N.; Dellis, P. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5799. (h) Qiu, L.; Wu, J.; Chan, S.; Au-Yeung, T. T.-L.; Ji, J.-X.; Guo, R.; Pai, C.-C.; Zhou, Z.; Li, X.; Fan, Q.-H.; Chan, A. S. C. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5815. (i) Qiu, L.; Kwong, F. Y.; Wu, J.; Lam, W. H.; Chan, S.; Yu, W.-Y.; Li, Y.-M.; Guo, R.; Zhou, Z.; Chan, A. S. C. J. Am. Chem. Soc. 2006, 128, 5955. (j) Boaz, N. W.; Mackenzie, E. B.; Debenham, S. D.; Large, S. E.; Ponasik, J. A. J. Org. Chem. 2005, 70, 1872. (k) Wang, C.-J.; Sun, X.; Zhang, X. Synlett 2006, 1169. (l) Sun, X.; Zhou, L.; Li, W.; Zhang, X. J. Org. Chem. 2008, 73, 1143.
[39]. Li, L.-S.; Wu, Y.-L. Tetrahedron Lett. 2002, 43, 2427-2430.
[40]. (a) Patel, D. V.; Rielly, G. K.; Ryono, D. E.; Free, C. A.; Smith, S. A.; Petrillo, Jr. E. W. J. Med. Chem. 1993, 36, 2431-2447; (b) Ocain, T.; Rich, D. H. J. Med. Chem. 1992, 35, 451-456; (c) Iwanowicz, E. J.; Lin, J.; Roberts, D. G. M.; Michel, I. M.; Seiler, S. M. Bioorg. Med. Chem. Lett. 1992, 2, 1607-1612; (d) Angelastro, M. R.; Mehdi, S.; Burkhart, J. P.; Peet, N. P.; Bey, P. J. Med. Chem. 1990, 33, 11-13.
[41]. (a) Yuan, W.; Wong, C.-H.; Haeggstroem, J. Z.; Wetterholm, A.; Samuelsson, B. J. Am. Chem. Soc. 1992, 114, 6552-6553; (b) Yuan, W.; Munoz, B.; Wong, C.-H.; Haeggstroem, J. Z.; Wetterholm, A.; Samuelsson, B. J. Med. Chem. 1993, 36, 211-220.
[42]. Photis, J. M. Tetrahedron Lett. 1980, 21, 3539-3540.
[43]. Valentine, D. Jr.; Scott, J. W. Synthesis 1978, 329-356.
[44]. Schulte, K.; Meinzinger, E. Ger. 949,521, 1956; Chem. Abstr. 1958, 52, 19024c.
[45]. (a) Yamada, K.; Kato, M.; Iyoda, M.; Hirata, Y. J. Chem. Soc., Chem. Commun. 1973, 499-500; (b) Burkhart, J. P.; Peet, N. P.; Bey, P. Tetrahedron Lett. 1988, 29, 3433-3436.
[46]. Micetich, R. G. Org. Prep. Proced. Int. 1970, 2, 249-252.
[47]. Wasserman, H. H.; Ho, W.-B. J. Org. Chem. 1994, 59, 4364-4366.
[48]. Singh, J.; Kissick, T. P.; Mueller, R. H. Org. Prep. Proced. Int. 1989, 21, 501-510.
[49]. Corey, E. J.; Erickson, B. W. J. Org. Chem. 1971, 36, 3553-3560.
[50]. Babudri, F.; Fiandanese, V.; Marchese, G.; Punzi, A. Tetrahedron 1996, 52, 13513-13520 and references cited therein.
[51].李裕林,李绍白.高等学校化学学报1983, 4(3): 389-391.
[52]. Singh J.,Thomas P. K., Richard H. M.. Org. Prep. Proced. Int. 1989, 21(4): 501-504
[53]. Ma Ming, Li, C.-K., Peng, L.-L., Xie Fang, Zhang Xiu and Wang J-B, Tetrahedron Lett. 2005, 46, 3927-3929.
[54]. (a) Stocks, M. J.; Harrison, R. P.; Teague, S. J. Tetrahedron Lett. 1995, 36, 6555-6558; (b) Pirrung, M. C.; Tepper, R. J. J. Org. Chem. 1995, 60, 2461-2465. (c) Chen, Y.-T.; Onaran, M. B.; Doss, C. J.; Seto, C. T. Bioorg. Med. Chem. Lett. 2001, 11, 1935-1938; (d) Beebe, X.; Nilius, A. M.; Merta, P. J.; Soni, N. B.; Bui M. H.; Wagner. R.; Beutel, B. A. Bioorg. Med. Chem. Lett. 2003, 13, 3133-3136.
[55]. (a) Hanessian, S. Total Synthesis of Natural Products: The Chiron Approach; Pergamon Press: New York, 1983. (b) Seuring, B.; Seebach, D. Helv. Chim. Acta 1977, 60, 1175. (c) Mori, K.; Takigawa, T.; Matsuo, T. Tetrahedron 1979, 35, 933.
[56]. (a) Orito, Y.; Imai, S.; Niwa, S. Nippon Kagaku Kaishi 1979, 1118. (b) Orito, Y.; Imai, S.; Niwa, S. Nippon Kagaku Kaishi 1980, 670. (c) Orito, Y.; Imai, S.; Niwa, S. Nippon Kagaku Kaishi 1982, 137. (d) Blaser, H.-U.; Jalett, H. P.; Wiehl, J. J. Mol. Catal. 1991, 68, 215. (e) Spindler, F.; Pittelkow, U.; Blaser, H.-U. Chirality 1991, 3, 370. (f) Blaser, H.-U.; Jalett, H. P.; Spindler, F. J. Mol. Catal. 1996, 107, 85. (g) Blaser, H.-U.; Müller, M. Stud. Surf. Sci. Catal. 1991, 59, 73. (h) Webb, G.; Wells, P. B. Catal. Today 1992, 12, 319. (i) Augustine, R. L.; Tanieylan, S. K.; Doyle, L. K. Tetrahedron: Asymmetry 1993, 4, 1803. (j) Wang, G.; Heinz, T.; Pfaltz, A.; Minder, B.; Mallat, T.; Baiker, A. J. Chem. Soc., Chem.Commun. 1994, 2047. (k) Minder, P.; Schurch, M.; Mallat, T.; Baiker, A.; Heinz, T.; Pfaltz, A. J. Catal. 1996, 160, 261.
[57]. (a) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029; and references cited therein. (b) Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. (c) Chiba, T.; Miyashita, A.; Nohira, H.; Takaya, H. Tetrahedron Lett. 1993, 34, 2351. (d) Genet, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Bischoff, L.; Cano De Andrade, M. C.; Darses, S.; Galopin, C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 675. (e) Benincori, T.; Brenna, E.; Sannicolo, F.; Trimarco, L.; Antognazza, P.; Cesarotti, E.; Demartin, F.; Pilati, T. J. Org. Chem. 1996, 61, 6244. (f) Benincori, T.; Cesarotti, E.; Piccolo, O.; Sannicolo, F. J. Org. Chem. 2000, 65, 2043.
[58]. (a) Zhang, W.; Adachi, Y.; Hirao, T.; Ikeda, I. Tetrahedron: Asymmetry 1996, 7, 451-460. (b) Zhang, W.; Hirao, T.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545-4548.
[59]. (a) Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1996, 37, 7995-7998. (b) Zhang, W.; Shimanuki, T.; Kida, T.; Nakatsuji, Y.; Ikeda, I. J. Org. Chem. 1999, 64, 6247-6251.
[60]. (a) Kang, J., Lee, J., Ahn, A., Choi, J. Tetrahedron Lett. 1998, 39, 5523-5526. (b) Kang, J., Lee, J., Kim, J., Kim, G., Chirality, 2000, 12, 378-382.
[61]. (a) Ogihara, T.; Nakamaru, M.; Higaki, J.; Kumahara, Y.; Hamano, Y.; Minamino, T.; Nakamura, N. Curr. Ther. Res. 1987, 41, 809. (b) Miyake, A.; Itoh, K.; Oka, Y. Chem. Pharm. Bull. 1986, 34, 2852.
[62]. Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7933.
[63]. (a) T. Saito. U.S. Patent 5,872,273, 1999; (b) T. Saito; T. Yokozawa; T. Ishizaki; T. Moroi; N. Sayo; T. Miura; H. Kumobayashi, Adv. Synth. Catal. 2001, 343, 264; (c) Z. Zhang; H. Qian; J. Longmire; X. Zhang, J. Org. Chem. 2000, 65, 6223; (d) S. Wu; W. Wang; W. Tang; M. Lin; X. Zhang, Org. Lett. 2002, 4, 4495;(e) C.-C. Pai; Y.-M. Li; Z.-Y. Zhou; A. S. C. Chan, Tetrahedron Lett. 2002, 43, 2789.
[64]. Zhang, Z.; Qian, H.; Longmire, J.; Zhang, X. J. Org. Chem. 2000, 65,6223-6226.
[65]. Ohwada, T.; Shudo, K. J. Org. Chem. 1989, 54, 5227-5237.
[66]. Cohen, M. J.; McNelis, E. J. Org. Chem. 1984, 49, 515-518.
[67]. Kolasa, T.; Miller, M. J. J. Org. Chem. 1987, 52, 4978-4884.
[68]. Hjelmencrantz, A.; Berg, U. J. Org. Chem. 2002, 67, 3585-3594.
[69]. Muller, A. J.; Nishiyama, K.; Griffin, G. W.; Ishikawa, K.; Gibson, D. M. J. Org. Chem. 1982, 47, 2342-2352.
[70]. Katritzky, A. R.; Wang, Z.; Wells, A. P.; Steel, P. J. Org. Prep. Proced. Int. 1995, 27, 457-462.
[71]. Fokas, D.; Patterson, J. E.; Slobodkin, G.; Baldino, C. M. Tetrahedron Lett. 2003, 44, 5137-5140.