Chiral ligands derived from abrine. Part 5: Substituent effects on asymmetric induction in enantioselective addition of diethylzinc to benzaldehyde catalyzed by chiral oxazolidines possessing an indole moiety

Tetrahedron Asymmetry

Volumn 9, Issue 16, 1998, Pages 2879-2888

  Zhu, Hua Jie ^a   Zhao, Bi Tao ^a   Dai, Wei Min ^b   Zhou, Jun ^a   Hao, Xiao Jiang ^a  

^a KUNMING INSTITUTE OF BOTANY   (China)

^b HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

BENZALDEHYDE; DIETHYLZINC; INDOLE DERIVATIVE; LIGAND; N METHYLTRYPTOPHAN; OXAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ABRUS; ARTICLE; CATALYSIS; CHIRALITY; ENANTIOMER; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032555558     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00298-5     Document Type: Article

References (32)

1. (a) Oguni, N.; Omi, T. Tetrahedron Lett. 1984, 25, 2823.
2. (b) Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071.
3. For reviews, see: (c) Noyori, R.; Kitamura, M. Angew. Chem. Int. Ed. Engl. 1991, 30, 49.
4. (d) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833.
5. (e) Oguni, N. Kikan Kagaku Sosetsu 1993, No. 19, 143.
6. (a) Dosa, P. I.; Fu, G. C. J. Am. Chem. Soc. 1998, 120, 445.
7. (b) Ramón, D. J.; Yus, M. Tetrahedron Lett. 1998, 39, 1239.
8. Phosphinoylimines, see: (a) Soai, K.; Suzuki, T.; Shono, T. J. Chem. Soc., Chem. Commun. 1994, 317. (b) Suzuki, T.; Narisada, N.; Shibata, T.; Soai, K. Tetrahedron: Asymmetry 1996, 7, 2519. (c) Suzuki, T.; Shibata, T.; Soai, K.; J. Chem. Soc., Perkin Trans. 1 1997, 2757. (d) Hayase, T.; Osanai, S.; Shibata, T.; Soai, K. Heterocycles 1998, 48, 139. (e) Andersson, P. G.; Guijarro, D.; Tanner, D. J. Org. Chem. 1997, 62, 7364. 3,4-Dihydroisoquinoline N-oxides, see: (f) Ukaji, Y.; Kenmoku, Y.; Inomata, K. Tetrahedron: Asymmetry 1996, 7, 53.
9. Phosphinoylimines, see: (a) Soai, K.; Suzuki, T.; Shono, T. J. Chem. Soc., Chem. Commun. 1994, 317. (b) Suzuki, T.; Narisada, N.; Shibata, T.; Soai, K. Tetrahedron: Asymmetry 1996, 7, 2519. (c) Suzuki, T.; Shibata, T.; Soai, K.; J. Chem. Soc., Perkin Trans. 1 1997, 2757. (d) Hayase, T.; Osanai, S.; Shibata, T.; Soai, K. Heterocycles 1998, 48, 139. (e) Andersson, P. G.; Guijarro, D.; Tanner, D. J. Org. Chem. 1997, 62, 7364. 3,4-Dihydroisoquinoline N-oxides, see: (f) Ukaji, Y.; Kenmoku, Y.; Inomata, K. Tetrahedron: Asymmetry 1996, 7, 53.
10. Phosphinoylimines, see: (a) Soai, K.; Suzuki, T.; Shono, T. J. Chem. Soc., Chem. Commun. 1994, 317. (b) Suzuki, T.; Narisada, N.; Shibata, T.; Soai, K. Tetrahedron: Asymmetry 1996, 7, 2519. (c) Suzuki, T.; Shibata, T.; Soai, K.; J. Chem. Soc., Perkin Trans. 1 1997, 2757. (d) Hayase, T.; Osanai, S.; Shibata, T.; Soai, K. Heterocycles 1998, 48, 139. (e) Andersson, P. G.; Guijarro, D.; Tanner, D. J. Org. Chem. 1997, 62, 7364. 3,4-Dihydroisoquinoline N-oxides, see: (f) Ukaji, Y.; Kenmoku, Y.; Inomata, K. Tetrahedron: Asymmetry 1996, 7, 53.
11. Phosphinoylimines, see: (a) Soai, K.; Suzuki, T.; Shono, T. J. Chem. Soc., Chem. Commun. 1994, 317. (b) Suzuki, T.; Narisada, N.; Shibata, T.; Soai, K. Tetrahedron: Asymmetry 1996, 7, 2519. (c) Suzuki, T.; Shibata, T.; Soai, K.; J. Chem. Soc., Perkin Trans. 1 1997, 2757. (d) Hayase, T.; Osanai, S.; Shibata, T.; Soai, K. Heterocycles 1998, 48, 139. (e) Andersson, P. G.; Guijarro, D.; Tanner, D. J. Org. Chem. 1997, 62, 7364. 3,4-Dihydroisoquinoline N-oxides, see: (f) Ukaji, Y.; Kenmoku, Y.; Inomata, K. Tetrahedron: Asymmetry 1996, 7, 53.
12. Phosphinoylimines, see: (a) Soai, K.; Suzuki, T.; Shono, T. J. Chem. Soc., Chem. Commun. 1994, 317. (b) Suzuki, T.; Narisada, N.; Shibata, T.; Soai, K. Tetrahedron: Asymmetry 1996, 7, 2519. (c) Suzuki, T.; Shibata, T.; Soai, K.; J. Chem. Soc., Perkin Trans. 1 1997, 2757. (d) Hayase, T.; Osanai, S.; Shibata, T.; Soai, K. Heterocycles 1998, 48, 139. (e) Andersson, P. G.; Guijarro, D.; Tanner, D. J. Org. Chem. 1997, 62, 7364. 3,4-Dihydroisoquinoline N-oxides, see: (f) Ukaji, Y.; Kenmoku, Y.; Inomata, K. Tetrahedron: Asymmetry 1996, 7, 53.
13. Phosphinoylimines, see: (a) Soai, K.; Suzuki, T.; Shono, T. J. Chem. Soc., Chem. Commun. 1994, 317. (b) Suzuki, T.; Narisada, N.; Shibata, T.; Soai, K. Tetrahedron: Asymmetry 1996, 7, 2519. (c) Suzuki, T.; Shibata, T.; Soai, K.; J. Chem. Soc., Perkin Trans. 1 1997, 2757. (d) Hayase, T.; Osanai, S.; Shibata, T.; Soai, K. Heterocycles 1998, 48, 139. (e) Andersson, P. G.; Guijarro, D.; Tanner, D. J. Org. Chem. 1997, 62, 7364. 3,4-Dihydroisoquinoline N-oxides, see: (f) Ukaji, Y.; Kenmoku, Y.; Inomata, K. Tetrahedron: Asymmetry 1996, 7, 53.
14. (a) Dai, W.-M.; Zhu, H. J.; Hao, X.-J. Tetrahedron: Asymmetry 1995, 6, 1857.
15. (b) Dai, W.-M.; Zhu, H. J.; Hao, X.-J. Tetrahedron: Asymmetry 1996, 7, 1245.
16. (c) Dai, W.-M.; Zhu, H. J.; Hao, X.-J. Tetrahedron Lett. 1996, 37, 5971.
17. Dictionary of Organic Compounds, 5th edn; Buckingham, J., Ed.; Chapman and Hall: New York, 1982; p. 4084.
18. (R)-1-Phenyl-1-propanol, see: Soai, K.; Watanabe, M. Tetrahedron: Asymmetry 1991, 2, 97.
19. Chiral piperazines: (a) Soai, K.; Niwa, S.; Yamada, Y.; Inoue, H. Tetrahedron Lett. 1987, 28, 4841. (b) Niwa, S.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1991, 2717. (c) Shono, T.; Kise, N.; Shirakawa, E.; Matsumoto, H.; Okazaki, E. J. Org. Chem. 1991, 56, 3063. (d) Fuji, K.; Tanaka, K.; Miyamoto, H. Chem. Pharm. Bull. 1993, 41, 1557.
20. Chiral piperazines: (a) Soai, K.; Niwa, S.; Yamada, Y.; Inoue, H. Tetrahedron Lett. 1987, 28, 4841. (b) Niwa, S.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1991, 2717. (c) Shono, T.; Kise, N.; Shirakawa, E.; Matsumoto, H.; Okazaki, E. J. Org. Chem. 1991, 56, 3063. (d) Fuji, K.; Tanaka, K.; Miyamoto, H. Chem. Pharm. Bull. 1993, 41, 1557.
21. Chiral piperazines: (a) Soai, K.; Niwa, S.; Yamada, Y.; Inoue, H. Tetrahedron Lett. 1987, 28, 4841. (b) Niwa, S.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1991, 2717. (c) Shono, T.; Kise, N.; Shirakawa, E.; Matsumoto, H.; Okazaki, E. J. Org. Chem. 1991, 56, 3063. (d) Fuji, K.; Tanaka, K.; Miyamoto, H. Chem. Pharm. Bull. 1993, 41, 1557.
22. Chiral piperazines: (a) Soai, K.; Niwa, S.; Yamada, Y.; Inoue, H. Tetrahedron Lett. 1987, 28, 4841. (b) Niwa, S.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1991, 2717. (c) Shono, T.; Kise, N.; Shirakawa, E.; Matsumoto, H.; Okazaki, E. J. Org. Chem. 1991, 56, 3063. (d) Fuji, K.; Tanaka, K.; Miyamoto, H. Chem. Pharm. Bull. 1993, 41, 1557.
23. Chiral pyrrolidine derivatives: (a) Chelucci, G.; Falorni, M.; Giacomelli, G. Tetrahedron: Asymmetry 1990, 1, 843. (b) Chelucci, G.; Conti, S.; Falorni, M.; Giacomelli, G. Tetrahedron 1991,47, 8251. (c) Asami, M.; Inoue, S. Bull. Chem. Soc. Jpn 1997, 70, 1687.
24. Chiral pyrrolidine derivatives: (a) Chelucci, G.; Falorni, M.; Giacomelli, G. Tetrahedron: Asymmetry 1990, 1, 843. (b) Chelucci, G.; Conti, S.; Falorni, M.; Giacomelli, G. Tetrahedron 1991,47, 8251. (c) Asami, M.; Inoue, S. Bull. Chem. Soc. Jpn 1997, 70, 1687.
25. Chiral pyrrolidine derivatives: (a) Chelucci, G.; Falorni, M.; Giacomelli, G. Tetrahedron: Asymmetry 1990, 1, 843. (b) Chelucci, G.; Conti, S.; Falorni, M.; Giacomelli, G. Tetrahedron 1991,47, 8251. (c) Asami, M.; Inoue, S. Bull. Chem. Soc. Jpn 1997, 70, 1687.
26. Other chiral diamines: (a) Rosini, C.; Franzini, L.; Iuliano, A.; Pini, D.; Salvadori, P. Tetrahedron: Asymmetry 1991, 2, 363. (b) Pini, D.; Mastantuono, A.; Uccello-Barretta, G.; Iuliano, A.; Salvadori, P. Tetrahedron 1993, 49, 9613. (c) Eilers, J.; Wilken, J.; Martens, J. Tetrahedron: Asymmetry 1996, 7, 2343.
27. Other chiral diamines: (a) Rosini, C.; Franzini, L.; Iuliano, A.; Pini, D.; Salvadori, P. Tetrahedron: Asymmetry 1991, 2, 363. (b) Pini, D.; Mastantuono, A.; Uccello-Barretta, G.; Iuliano, A.; Salvadori, P. Tetrahedron 1993, 49, 9613. (c) Eilers, J.; Wilken, J.; Martens, J. Tetrahedron: Asymmetry 1996, 7, 2343.
28. Other chiral diamines: (a) Rosini, C.; Franzini, L.; Iuliano, A.; Pini, D.; Salvadori, P. Tetrahedron: Asymmetry 1991, 2, 363. (b) Pini, D.; Mastantuono, A.; Uccello-Barretta, G.; Iuliano, A.; Salvadori, P. Tetrahedron 1993, 49, 9613. (c) Eilers, J.; Wilken, J.; Martens, J. Tetrahedron: Asymmetry 1996, 7, 2343.
29. Zinc amides of chiral oxazolidines, see: Prasad, K. R. K.; Joshi, N. N. J. Org. Chem. 1997, 62, 3770.
30. 2Zn, see: (a) Tanaka, K.; Oshio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. (b) Ref. 9b.
31. 2Zn, see: (a) Tanaka, K.; Oshio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. (b) Ref. 9b.
32. a values in DMSO of 44 and 21.0 were reported for pyrrolidine and indole, respectively, see: Bordwell, F. G.; Drucker, G. E.; Fried, H. E. J. Org. Chem. 1981, 46, 632.