Enantioselective addition of diethylzinc to aldehydes catalyzed by a new chiral β-amino alcohol derived from D-mannitol

Tetrahedron Asymmetry

Volumn 9, Issue 9, 1998, Pages 1489-1492

  Cho, Byung Tae ^a   Chun, Yu Sung ^a  

^a Hallym University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE; MANNITOL; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOSPECIFICITY;

EID: 0000115873     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00143-8     Document Type: Article

References (26)

1. For reviews, see (a) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833-856 and references cited therein; (b) Noyori, R.; Kitamura, M. Angew. Chem. Int. Ed. Eng. 1991, 30, 49-69; (c) Noyori, R.; Kitamura, M. In Modern Synthetic Methods; Ed. Scheffold, R. Springer-Verlag, 1989; pp. 115-198; (d) Knochel, P. In Comprehensive Organic Synthesis; Ed. Trost, B. M. Pergamon Press, 1991; pp. 211-229.
2. For reviews, see (a) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833-856 and references cited therein; (b) Noyori, R.; Kitamura, M. Angew. Chem. Int. Ed. Eng. 1991, 30, 49-69; (c) Noyori, R.; Kitamura, M. In Modern Synthetic Methods; Ed. Scheffold, R. Springer-Verlag, 1989; pp. 115-198; (d) Knochel, P. In Comprehensive Organic Synthesis; Ed. Trost, B. M. Pergamon Press, 1991; pp. 211-229.
3. For reviews, see (a) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833-856 and references cited therein; (b) Noyori, R.; Kitamura, M. Angew. Chem. Int. Ed. Eng. 1991, 30, 49-69; (c) Noyori, R.; Kitamura, M. In Modern Synthetic Methods; Ed. Scheffold, R. Springer-Verlag, 1989; pp. 115-198; (d) Knochel, P. In Comprehensive Organic Synthesis; Ed. Trost, B. M. Pergamon Press, 1991; pp. 211-229.
4. For reviews, see (a) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833-856 and references cited therein; (b) Noyori, R.; Kitamura, M. Angew. Chem. Int. Ed. Eng. 1991, 30, 49-69; (c) Noyori, R.; Kitamura, M. In Modern Synthetic Methods; Ed. Scheffold, R. Springer-Verlag, 1989; pp. 115-198; (d) Knochel, P. In Comprehensive Organic Synthesis; Ed. Trost, B. M. Pergamon Press, 1991; pp. 211-229.
5. (a) Kang, J.; Kim, J. W.; Lee, J. W.; Kim, D. S.; Kim, J. I. Bull. Korean Chem. Soc. 1996, 17, 1135-1142;
6. (b) Bolm, C.; Schlingloff, G.; Harms, K. Chem. Ber. 1992, 125, 1191-1203;
7. (c) Soai, K.; Hayase, T.; Takai, K.; Sugiyama, T. J. Org. Chem. 1994, 59, 7908-7909;
8. (d) Soai, K.; Hirose, Y.; Ohno, Y. Tetrahedron: Asymmetry, 1993, 4, 1473-1474;
9. (e) Delair, P.; Einhorn, C.; Einhorn, J.; Luche, J. L. Tetrahedron 1995, 51, 165-172;
10. (f) Belliczey, J.; Giffels, G.; Kragl, U.; Wandry, C. Tetrahedron: Asymmetry 1997, 8, 1529-1530;
11. (g) Dosa, P. L.; Ruble, J. C.; Fu, G. C. J. Org. Chem. 1997, 62, 444-445;
12. (h) Prasad, K. R. K.; Joshi, N. N. J. Org. Chem. 1997, 62, 3770-3771.
13. (a) Cho, B. T.; Kim, N. Tetrahedron Lett. 1994, 35, 4115-4118;
14. (b) Cho, B. T.; Kim, N.; Khoo, J.-H. Bull. Korean Chem. Soc. 1996, 17, 1-2;
15. (c) Cho, B. T.; Kim, N. Bull. Korean Chem. Soc. 1994, 15, 931-932;
16. (d) Cho, B. T.; Kim, N. Synth. Commun. 1995, 25, 167-175;
17. (e) Cho, B. T.; Kim, N. J. Chem. Soc., Perkin Trans. 1. 1996, 2901-2907.
18. Cho, B. T.; Kim, N. Synth. Commun. 1996, 26, 855-865.
19. Cho, B. T.; Kim, N. Synth. Commun. 1996, 26, 2273-2280.
20. (a) Soai, K.; Yokoyama, S.; Hayasaka, T. J. Org. Chem. 1991, 56, 4264-4268;
21. (b) Soai, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111-7115.
22. 5: C, 69.23; H, 11.41; N, 2.88. Found: C, 69.11; H, 11.59; N,2.64.
23. (a) Kim, B. H.; Sharpless, K. B. Tetrahedron Lett. 1989, 30, 655-658;
24. (b) Baker, B. R.; Haines, A. H. J. Org. Chem. 1963, 28, 442-445.
25. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543-2549. MTPA=α-methoxy-α-(trifluoromethyl)-phenylacetic acid.
26. Westley, J. W.; Halpern, B. J. Org. Chem. 1968, 33, 3978-3980.