Chiral pyrrolidine derivatives as catalysts in the enantioselective addition of diethylzinc to aldehydes

Tetrahedron Asymmetry

Volumn 10, Issue 1, 1999, Pages 133-138

  Yang, Xiaowu ^a   Shen, Jianheng ^a   Da, Chaoshan ^a   Wang, Rui ^a   Choi, Michael C K ^b   Yang, Liwei ^b   Wong, Kwok Yin ^b  

^a LANZHOU UNIVERSITY   (China)

^b HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; PYRROLIDINE DERIVATIVE; ZINC DERIVATIVE;

ARTICLE; CATALYST; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; STEREOSPECIFICITY;

EID: 0033556515     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00497-2     Document Type: Article

References (42)

1. (a) Qian, Y. L.; Chan, A. S. C. Organometallic Chemistry and Catalysis; Chemical Industry Press: Beijing, 1997; pp. 107-264.
2. (b) Corey, E. J.; Guzman-Perze, A. Angew. Chem., Int. Ed. Engl. 1998, 37, 388-401.
3. (c) Chan, A. S. C.; Zhang, F. Y.; Yip, C. W. J. Am. Chem. Soc. 1997, 119, 4080-4081.
4. (d) Wang, R.; Yang, X. W. Huaxue 1996, 54, 169-182.
5. For reviews, see: (a) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49-69. (b) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833-856. (c) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117-2188.
6. For reviews, see: (a) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49-69. (b) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833-856. (c) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117-2188.
7. For reviews, see: (a) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49-69. (b) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833-856. (c) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117-2188.
8. (a) Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071-6072.
9. (b) Soai, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111-7115.
10. (c) Dai, W. M.; Zhu, H. J.; Hao, X. J. Tetrahedron: Asymmetry 1996, 7, 1245-1248.
11. (d) Bringmann, G.; Breuning, M. Tetrahedron: Asymmetry 1998, 9, 667-679.
12. (e) Cho, B. T.; Chun, Y. S. Tetrahedron: Asymmetry 1998, 9, 1489-1492.
13. (a) Anderson, J. C.; Harding, M. Chem. Commun. 1998, 393-394.
14. (b) Rijinberg, E.; Jastrzebsk, J.; Janssen, M. D.; Boersma, J.; van Koten, G. Tetrahedron Lett. 1994, 35, 6521-6524.
15. (a) Bolm, C.; Zehnder, M.; Bur, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 205-207.
16. (b) Ishizaki, M.; Fujita, K.; Shimamoto, M.; Hoshino, O. Tetrahedron: Asymmetry 1994, 5, 411-424.
17. (a) Chelucci, G.; Conti, S.; Falorni, M.; Giacomelli, G. Tetrahedron 1991, 47, 8251-8258.
18. (b) Conti, S.; Falorni, M.; Giacomelli, G.; Soccolini, F. Tetrahedron 1992, 48, 8993-9000.
19. (a) Zhang, F. Y.; Chan, A. S. C. Tetrahedron: Asymmetry 1997, 8, 3651-3655.
20. (b) Zhang, F. Y.; Yip, C. W.; Cao, R.; Chan, A. S. C. Tetrahedron: Asymmetry 1997, 8, 585-589.
21. (c) Seebach, D.; Beck, A. K.; Schmidt, B.; Wang, Y. M. Tetrahedron 1994, 50, 4363-4384.
22. (d) Weber, B.; Seebach, D. Tetrahedron 1994, 50, 7473-7484.
23. (e) Schmidt, B.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 1321-1323.
24. (f) Rheiner, P. B.; Sellner, H.; Seebach, D. Helv. Chim. Acta. 1997, 80, 2027-2032.
25. (a) Soai, K.; Yokoyama, S.; Hayasaka, T. J. Org. Chem. 1991, 56, 4264-4268.
26. (b) Kitamura, M.; Okada, S.; Suga, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028-4036.
27. (c) Guo, C.; Qiu, J.; Zhang, X. M. Tetrahedron 1997, 53, 4145-4158.
28. (d) Mehler, T.; Martens, J. Tetrahedron: Asymmetry 1994, 5, 207-210.
29. (e) Fitzpatrick, K.; Hulst, R.; Kellogg, R. M. Tetrahedron: Asymmetry 1995, 6, 1861-1864.
30. (f) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233-5236.
31. For the synthesis of chiral β-amino alcohol moieties 1-7, see: (a) Wang, R.; Yang, X. W.; Jia, Q.; Ni, J. M. Progress in Natural Science 1998, 8, 238-243. (b) Yang, X. W.; Wang, R.; Ni, J. M. Chem. J. Chin. Univ. 1997, 18, 911-913. (c) Ender, D.; Kipphardt, H.; Gerdes, P.; Brenavalle, L. J. Bull. Soc. Chim. Belg. 1988, 97, 691-704.
32. For the synthesis of chiral β-amino alcohol moieties 1-7, see: (a) Wang, R.; Yang, X. W.; Jia, Q.; Ni, J. M. Progress in Natural Science 1998, 8, 238-243. (b) Yang, X. W.; Wang, R.; Ni, J. M. Chem. J. Chin. Univ. 1997, 18, 911-913. (c) Ender, D.; Kipphardt, H.; Gerdes, P.; Brenavalle, L. J. Bull. Soc. Chim. Belg. 1988, 97, 691-704.
33. For the synthesis of chiral β-amino alcohol moieties 1-7, see: (a) Wang, R.; Yang, X. W.; Jia, Q.; Ni, J. M. Progress in Natural Science 1998, 8, 238-243. (b) Yang, X. W.; Wang, R.; Ni, J. M. Chem. J. Chin. Univ. 1997, 18, 911-913. (c) Ender, D.; Kipphardt, H.; Gerdes, P.; Brenavalle, L. J. Bull. Soc. Chim. Belg. 1988, 97, 691-704.
34. Soai, K.; Watanabe, M. Tetrahedron: Asymmetry 1991, 2, 97-100.
35. (a) Kitamura, M.; Yamakawa, M.; Oka, H.; Suga, S.; Noyori, R. Chem. Eur. J. 1996, 2, 1173-1181.
36. (b) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5237-5240.
37. (a) Yasuda, H.; Ohnuma, Y.; Nakamura, A.; Kai, Y.; Yasuoka, N.; Kasai, N. Bull. Chem. Soc. Jpn. 1980, 53, 1101-1111.
38. (b) Dewar, M. J. S.; Merz Jr., K. M. Organometallics 1988, 7, 522-524.
39. Soai, K.; Watanabe, M.; Koyano, M. Bull. Chem. Soc. Jpn. 1989, 62, 2124-2125.
40. (a) Yang, X. W.; Wang, R. Tetrahedron: Asymmetry 1997, 8, 3275-3281.
41. (b) Fuji, K.; Mode, M.; Nagasawa, H.; Naniwa, Y.; Taga, T.; Machida, K.; Snatzke, G. J. Am. Chem. Soc. 1989, 111, 7921-7925.
42. (c) Falorni, M.; Collu, C.; Conti, S.; Giacomelli, G. Tetrahedron: Asymmetry 1996, 7, 293-299.