Kinetic resolution of propargylic alcohols catalyzed by benzotetramisole

Organic Letters

Volumn 8, Issue 21, 2006, Pages 4859-4861

  Birman, Vladimir B ^a   Guo, Lei ^a  

^a WASHINGTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; BENZOTETRAMISOLE; DRUG DERIVATIVE; TETRAMISOLE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS;

ALCOHOLS; CATALYSIS; KINETICS; MOLECULAR STRUCTURE; TETRAMISOLE;

EID: 33750308938     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061906y     Document Type: Article

References (26)

1. For recent reviews, see: (a) Vedejs, E.; Jure, M. Angew. Chem., Int. Ed. 2005, 44, 3974.
2. (b) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138.
3. (c) Jarvo, E. R.; Miller, S. J. Asymmetric Acylation. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, Heidelberg, 2004; Supplement 1, Chapter 43.
4. (a) Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794.
5. (b) Bellemin-Laponnaz, S.; Tweddell, J.; Ruble, J. C.; Breitling, F. M.; Fu, G. C. Chem. Commun. 2000, 1009.
6. (c) Tao, B.; Ruble, J. C.; Hoic, D. A.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 5091.
7. (d) Fu, G. C. Acc. Chem. Res. 2004, 37, 542.
8. (a) Vedejs, E.; Daugulis, O.; J. Am. Chem. Soc. 1999, 121, 5813.
9. (b) Vedejs, E.; MacKay J. A. Org. Lett. 2001, 3, 535.
10. (c) Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 2003, 125, 4166.
11. Spivey, A. C.; Fekner, T.; Spey, S. E. J. Org. Chem. 2000, 65, 3154.
12. (a) Birman, V. B.; Uffman, E. W.; Jiang, H.; Li, X.; Kilbane, C. J. J. Am. Chem. Soc. 2004, 126, 12226.
13. (b) Birman, V. B.; Jiang, H. Org. Lett. 2005, 7, 3445.
14. (c) Birman, V. B.; Li, X. Org. Lett. 2006, 8, 1351.
15. (d) Birman, V. B.; Jiang, H.; Li, X.; Guo, L.; Uffman, E. W. J. Am. Chem. Soc. 2006, 128, 6536.
16. Kano, T.; Sasaki, K.; Maruoka, K. Org. Lett. 2005, 7, 1347;
17. Yamada, S.; Misono, T.; Iwai, Y. Tetrahedron Lett. 2005, 46, 2239.
18. A single example (substrate 4a) reported in ref 7 proceeded with low selectivity (s = 6.6).
19. Efficient KR of propargylic alcohols can be achieved using enzymes. See, e.g.: (a) Burgess, K.; Jennings, L. D. J. Am. Chem. Soc. 1991, 113, 6129.
20. (b) Xu, D.; Li, Z.; Ma, S. Tetrahedron Lett. 2003, 44, 6343.
21. Enantioenriched propargylic alcohols are also prepared via asymmetric synthesis. For enantioselective alkynylation of aldehydes, see: (a) Pu, L. Tetrahedron 2003, 59, 9873 (review).
22. (b) Wolf, C.; Liu, S. J. Am. Chem. Soc. 2006, 128, 10996 (up-to-date list of references).
23. For enantioselective reduction of α,β-acetylenic ketones, see: (c) Midland, M. M.; McDowell, D. C.; Hatch, R. L.; Tramontano, A. J. Am. Chem. Soc. 1980, 102, 867.
24. (d) Brown, H. C.; Ramachandran, P. V.; Weissman, S. A.; Swaminathan, S. J. Org. Chem. 1990, 55, 6328.
25. (e) Matsumura, K.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 8738.
26. Selectivity factor is defined as s = k(fast-reacting enantiomer)/ k(slow-reacting enantiomer). See: Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249.