Advances in Proline-Catalyzed Asymmetric Reactions

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LI Jing-Wei, XU Li-Wen, XIA Chun-Gu. Advances in Proline-Catalyzed Asymmetric Reactions[J]. Chinese Journal of Organic Chemistry, 2004, 24(1): 23-28.

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1 Morrison, J. D. Asymmetric Synthesis, Vol. 5, Academic, Orlando, 1985.
2 Noyori, R. Asymmetric Catalysis in Organic Synthesis, Wiley,New York, 1994.
3 Qian, Y. L.; Chan, A. S. C. Organometallic Chemistry and Catalysis, Chinese Chemical Industry Press, Beijing, 1997 (inChinese).
(钱延龙, 陈新滋, 金属有机化学与催化, 化学工业出版社, 北京, 1997.)
4 Yin, Y. Q.; Jiang, Y. Z. Progress in Asymmetric Catalysis, Science Press, Beijing, 2000 (in Chinese).
(殷元骐, 蒋耀忠, 不对称催化反应进展, 科学出版社, 北京, 2000.)
5 Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H. Comprehensive Asymmetric Catalysis I～III, Springer, Berlin, 1999.
6 For recently notable examples of organocatalytic reactions, see: Mannich reaction:
(a) Cordova, A.; Barbas, C. F. Tetrahedron Lett. 2003, 44, 1923.
Polymerization reaction:
(b) Connor, E. F.; Nyce, G. W.; Myers, M.; Mock, A.; Hedrick, J. L. J. Am. Chem. Soc. 2002, 124, 914.
Aldol reaction:
(c) Cordova, A.; Notz, W.; Barbas, C. F. Chem. Commun. 2002, 24, 3024.
(d) Dickerson, T. J.; Janda, K. D. J. Am. Chem. Soc. 2002, 124, 3220.
Diels-Alder reaction:
(e) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172.
(f) Selkala, S. A.; Tois, J.; Pihko, P. M.; Koskinen, A. M. P. Adv. Synth. Catal. 2002, 344, 941.
(g) Northrup, A. B.; MacMillan, D. W. C. Abstr. Pap. Am. Chem. S. 2002, 224, 879.
(h) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F. TetrahedronLett. 2002, 43, 6743.
(i) Northrup, A. B.; MacMillan, D. W.C. J. Am. Chem. Soc. 2002, 124, 2458.
Michael reaction:
(j) Brown, S. P.; MacMillan, D. W. C. Abstr. Pap. Am. Chem. S.2002, 224, 878.
(k) Takasu, K.; Maiti, S.; Ihara, M. Heterocycles 2003, 59, 51.
(l) Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192.
Addition reaction:
(m) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894.
(n) Paras, N. A.; MacMillan, D. W. C. Abstr. Pap. Am. Chem. S.2002, 224, 880.
(o) Halland, N.; Hazell, R. G.; Jorgensen, K. A. J. Org. Chem.2002, 67, 8331.
(p) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661.
7 For some excellent reviews on proline-catalyzed asymmetric reactions, see:
(a) List, B. Tetrahedron 2002, 58, 5573.
(b) List, B. Synlett 2001, 1675.
(c) Jarvo, E. R.; Miller, S. J. Tetrahedron 2002,58, 2481.
(d) Movassaghi, M.; Jacobsen, E. N. Science 2002,298, 1904.
For other notable articles on organocatalysis, see: Phosphorus:
(e) Buono, G.; Chiodi, O.; Wills, M. Synlett 1999,377.
Phase transfer catalysis:
(f) Zhang, F.-Y.; Corey, E. J. Org. Lett. 2000, 2, 1097.
Catalytic antibodies:
(g) Hilvert, D. Ann. Rev. Biochem. 2000, 69, 751.
Peptide catalysts:
(h) Horstmann, T. E.; Guerin, D. J.; Miller, S. J. Angew. Chem., Int. Ed. 2000, 39, 3635.
8 List, B.; Lerner, R.; Barbas III, C. F. J. Am. Chem. Soc. 2000, 122, 2395.
9 Mahrwald, R. Chem. Rev. 1999, 99, 1095.
10 Grøger, H.; Vogl, E. M.; Shibasaki, M. Chem. Eur. J. 1998, 4, 1137.
11 Nelson, S. G. Tetrahedron: Asymmetry 1998, 9,357.
12 Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417.
13 (a) Hajos, Z. G.; Parrish, D. R. DE 2102623, 1971 [Chem. Abstr. 1971, 75, 129414r].
(b) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615.
14 (a) Eder, U.; Sauer, G.; Wiechert, R. DE 2014757, 1971 [Chem. Abstr. 1972, 76, 14180q].
(b) Eder, U.; Sauer, G.; Wiechert, R. Angew.Chem., Int. Ed. Engl. 1971, 10, 496.
15 Rajagopal, D.; Rajagopan, K.; Swaminathan, S. Tetrahedron: Asymmetry 1996, 7, 2189.
16 List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001,3, 573.
17 Arno, M.; Domingo, L. R. Theor. Chem. Acc. 2002, 108, 232.
18 Kotrusz, P.; Kmentova, I.; Gotov, B.; Toma, S.; Solcaniova, E. Chem.Commun. 2002, 2510.
19 Izquierdo, I.; Plaza, M. T.; Robles, R.; Mota, A. J.; Franco, F. Tetrahedron: Asymmetry 2001, 12, 2749.
20 Bøgevig, A.; Gothelf, K. V.; Jørgensen, K. A. Chem.-Eur. J. 2002, 8, 5652.
21 Bøgevig, A.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun.2001, 620.
22 Cordova, A.; Notz, W.; Barbas III, C. F. J. Org. Chem. 2002, 67, 301.
23 Chowdari, N. S.; Ramachary, D. B.; Cordova, A.; Barbas III, C. F. Tetrahedron. Lett. 2002, 43, 9591.
24 Yamasaki, S.; Iida, T.; Shibaski, M. Tetrahedron Lett. 1999, 40, 307.
25 List, B. J. Am. Chem. Soc. 2000, 122, 9336.
26 Bergmeier, S. C. Tetrahedron 2000, 56, 2561.
27 List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827.
28 Sakthivel, K.; Bui, T.; Barbas III, C. F. J. Am. Chem. Soc. 2001, 123, 5260.
29 (a) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas III, C.F. J. Am. Chem. Soc. 2002, 124, 1842.
(b) Córdova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas III,C. F. J. Am. Chem. Soc. 2002, 124, 1866.
30 Jha, S. C.; Joshi, N. N. ARKIVOC 2002, Part 7, 167.
31 Yamaguchi, M.; Yokota, N.; Minami, T. J. Chem. Soc., Chem. Commun.1991, 1088.
32 Yamaguchi, M.; Shiraishi, T.; Hirama, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1176.
33 (a) Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233.
(b) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520.
(c) Yamaguchi, M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama, M. Tetrahedron 1997, 53, 11223.
34 Hanessian, S.; Pham, V. Org. Lett. 2000, 2,2975.
35 Kozikowski, A. P.; Mugrage, B. B. J. Org. Chem. 1989, 54, 2275.
36 Hirai, Y.; Takashi, T.; Yamazaki, T.; Momose, T. J. Chem. Soc., Perkin. Trans. 1 1992, 509.
37 List, B.; Pojarliev, P.; Martin, H. Org. Lett. 2001, 3, 2423.
38 Enders, D.; Seki, A. Synlett 2002, 26.
39 List, B.; Castello, C. Synlett 2001, 1687.
40 Ramamurthi, N.; Swaminathan, S. Indian J. Chem., Sect. B 1990, 29, 401.
41 Przezdziecka, A.; Stepanenko, W.; Wicha, J. Tetrahedron: Asymmetry1999, 10, 1589.
42 For some reviews on the electrophilic α-amination of aldehydes,see:
(a) Genet, J. P.; Greck, C.; Lavergne, D. In Modern Amination Methods, Ed.: Ricci, A., Wiley-VCH, Weinheim, 2000, Chapter 3.
(b) Krohn, K. In Organic Synthesis Highlights, Eds.: Mulzer,J.; Altenbach, H.-J.; Braun, M.; Krohn, K.; Reissig, H. U., VCH, Weinheim, 1991, pp. 45～53.
(c) Greck, C.; Genet, J. P. Synlett 1997, 741.
(d) Boche, G. In Stereoselective Synthesis, Vol. 9, Eds.: Helmchen, G.; Hoffmann, R. W.; Mulzer, J., Thieme, Stuttgart, 1996, pp. 5133～5157.
43 List, B. J. Am. Chem. Soc. 2002, 124, 5656.
44 Bøgevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790.
45 Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bøgevig, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254.
46 Ramachary, D. B.; Chowdari, N. S.; Barbas III, C. F. Tetrahedron Lett. 2002, 43, 6743.

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