Convenient preparation of chiral primary alcohols via catalytic asymmetric reduction of aldehydes using Bu3SnD

Journal of Organic Chemistry

Volumn 61, Issue 22, 1996, Pages 7638-7639

  Keck, Gary E ^a   Krishnamurthy, Dhileepkumar ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANOL;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; ISOTOPE LABELING; REACTION ANALYSIS; TECHNIQUE;

EID: 0029844609     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961593s     Document Type: Article

References (24)

1. (a) Floss, H. G.; Lee, S. Acc. Chem. Res. 1993, 26, 116.
2. (b) Parry, R. J.; Trainor, D. A. J. Am. Chem. Soc. 1978, 100, 5243.
3. (c) Kobayashi, K.; Jadhav, P. K.; Zydowsky, T. M.; Floss, H. G. J. Org. Chem. 1983, 48, 3510.
4. (d) Shibuga, M.; Chou, H.-M.; Fountoulakis, M.; Hassam, S.; Kim, S.-V.; Kobayashi, K.; Otsuka, H.; Rogalska, E.; Cassady, J. M.; Floss, H. G. J. Am. Chem. Soc. 1990, 112, 297.
5. (e) Mu, Y.; Omer, C. A.; Gibbs, R. A. J. Am. Chem. Soc. 1996, 118, 1817.
6. We are aware of only one previous report on the catalytic asymmetric reduction of aldehydes: Corey, E. J.; Link, J. O. Tetrahedron Lett. 1989, 30, 6275.
7. (a) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467.
8. (b) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827.
9. (c) Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543.
10. (a) Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363.
11. (b) Keck, G. E.; Li, X.-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998.
12. (c) Descriptions of catalyst preparations herein are used as consistent with our previous reports.
13. The literature on this subject is extensive. For representative and leading references, see: (a) Tanner, D. D.; Singh, H. K. J. Org. Chem. 1986, 51, 5182. (b) Shibata, I.; Yoshida, T.; Kawakami, T.; Baba, A.; Matsuda, H. J. Org. Chem. 1992, 57, 4049. (c) Zelechonok, Y.; Silverman, R. B. J. Org. Chem. 1992, 57, 5785. (d) Vedejs, E.; Duncan, S. M.; Haight, A. R. J. Org. Chem. 1993, 58, 3046. (e) Hays, D. S.; Fu, G. C. J. Org. Chem. 1996, 61, 4.
14. The literature on this subject is extensive. For representative and leading references, see: (a) Tanner, D. D.; Singh, H. K. J. Org. Chem. 1986, 51, 5182. (b) Shibata, I.; Yoshida, T.; Kawakami, T.; Baba, A.; Matsuda, H. J. Org. Chem. 1992, 57, 4049. (c) Zelechonok, Y.; Silverman, R. B. J. Org. Chem. 1992, 57, 5785. (d) Vedejs, E.; Duncan, S. M.; Haight, A. R. J. Org. Chem. 1993, 58, 3046. (e) Hays, D. S.; Fu, G. C. J. Org. Chem. 1996, 61, 4.
15. The literature on this subject is extensive. For representative and leading references, see: (a) Tanner, D. D.; Singh, H. K. J. Org. Chem. 1986, 51, 5182. (b) Shibata, I.; Yoshida, T.; Kawakami, T.; Baba, A.; Matsuda, H. J. Org. Chem. 1992, 57, 4049. (c) Zelechonok, Y.; Silverman, R. B. J. Org. Chem. 1992, 57, 5785. (d) Vedejs, E.; Duncan, S. M.; Haight, A. R. J. Org. Chem. 1993, 58, 3046. (e) Hays, D. S.; Fu, G. C. J. Org. Chem. 1996, 61, 4.
16. The literature on this subject is extensive. For representative and leading references, see: (a) Tanner, D. D.; Singh, H. K. J. Org. Chem. 1986, 51, 5182. (b) Shibata, I.; Yoshida, T.; Kawakami, T.; Baba, A.; Matsuda, H. J. Org. Chem. 1992, 57, 4049. (c) Zelechonok, Y.; Silverman, R. B. J. Org. Chem. 1992, 57, 5785. (d) Vedejs, E.; Duncan, S. M.; Haight, A. R. J. Org. Chem. 1993, 58, 3046. (e) Hays, D. S.; Fu, G. C. J. Org. Chem. 1996, 61, 4.
17. The literature on this subject is extensive. For representative and leading references, see: (a) Tanner, D. D.; Singh, H. K. J. Org. Chem. 1986, 51, 5182. (b) Shibata, I.; Yoshida, T.; Kawakami, T.; Baba, A.; Matsuda, H. J. Org. Chem. 1992, 57, 4049. (c) Zelechonok, Y.; Silverman, R. B. J. Org. Chem. 1992, 57, 5785. (d) Vedejs, E.; Duncan, S. M.; Haight, A. R. J. Org. Chem. 1993, 58, 3046. (e) Hays, D. S.; Fu, G. C. J. Org. Chem. 1996, 61, 4.
18. (a) Midland, M. M.; Tramontano, A.; Zderic, S. A. J. Am. Chem. Soc. 1977, 99, 5211.
19. (b) Midland, M. M.; Greer, S.; Tramontano, A.; Zderic, S. A. J. Am. Chem. Soc. 1979, 101, 2352.
20. Still, W. C. J. Am. Chem. Soc. 1978, 100, 1481.
21. 3SnCl has also been described: Kühlein, K.; Neumann, W. P.; Mohring, H. Angew. Chem., Int. Ed. Engl. 1968, 7, 455.
22. Alternatively, resolution of racemic BINOL can be accomplished by a number of procedures; the procedure developed recently at Merck is particularly convenient: Cai, D.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1995, 36, 7991.
23. However, Brown and co-workers have reported procedures to increase the optical purity of pinene to essentially 100%: (a) Brown, H. C.; Yco, N. M. Isr. J. Chem. 1977, 15, 12. (b) Brown, H. C.; Singaram, B. J. Org. Chem. 1984, 49, 945.
24. However, Brown and co-workers have reported procedures to increase the optical purity of pinene to essentially 100%: (a) Brown, H. C.; Yco, N. M. Isr. J. Chem. 1977, 15, 12. (b) Brown, H. C.; Singaram, B. J. Org. Chem. 1984, 49, 945.