Lipase catalyzed kinetic resolution of aryl β-hydroxy ketones

Tetrahedron Asymmetry

Volumn 11, Issue 10, 2000, Pages 2049-2052

  Nair, Mangalam S ^a   Joly, S ^a  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL BETA HYDROXY KETONE; FUNGAL ENZYME; KETONE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; CANDIDA; CANDIDA CYLINDRACEA; CATALYSIS; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CONTROLLED STUDY; ENANTIOMER; ESTERIFICATION; PRIORITY JOURNAL; RACEMIC MIXTURE;

EID: 0034595847     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00159-2     Document Type: Article

References (22)

1. (a) Narasaka, K.; Pai, F. C. Tetrahedron 1984, 40, 2233.
2. (b) Evans, D. A.; Chapman, K. T.; Carrera, E. M. J. Am. Chem. Soc. 1988, 110, 3560.
3. Haddad, M.; Dorbais, J.; Larchevêque, M. Tetrahedron Lett. 1997, 38, 5981.
4. Masamune, S.; Choy, W.; Peterson, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1.
5. (a) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319 and references cited therein.
6. (b) Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649.
7. (c) Evans, D. A.; MacMillan, D. W. C.; Campos, K. R. J. Am. Chem. Soc. 1997, 119, 10859.
8. (d) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871.
9. Drauz, K.; Waldman, H. Enzyme Catalysis In Organic Synthesis; VCH: Weinheim, 1995; Vol. I and II.
10. Zhong, G.; Shabat, D.; List, B.; Anderson, J.; Sinha, S. C.; Lerner, R. A.; Barbas III, C. F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2481.
11. Adam, W.; Díaz, M. T.; Fell, R. T.; Saha-Möller, C. R. Tetrahedron: Asymmetry 1996, 7, 2207.
12. Master, H. E.; Newadkar, R. V.; Rane, R. A.; Kumar, A. Tetrahedron Lett. 1996, 37, 9253.
13. (a) Nair, M. S.; Anilkumar, A. T. Tetrahedron: Asymmetry 1996, 7, 511.
14. (b) Anilkumar, A. T.; Sudhir, U.; Joly, S.; Nair, M. S. Tetrahedron 2000, 56, 1899.
15. (a) Welch, W. M.; Kraska, A. R.; Sarges, R.; Coe, K. B. J. Med. Chem. 1984, 27, 1508.
16. (b) Coe, B. K.; Weissman, A.; Welch, W. M.; Broune, R. G. J. Pharmacol. Exp. Ther. 1983, 226, 686.
17. Tsuji, J.; Shimizu, I.; Yamamoto, K. Tetrahedron Lett. 1976, 17, 2975.
18. Wilson, S. R.; Guazzaroni, M. E. J. Org. Chem. 1989, 54, 3087.
19. Shokat, K.; Uno, T.; Schultz, P. G. J. Am. Chem. Soc. 1994, 116, 2261.
20. The other isomer is not seen in 300 MHz NMR. Since NMR technique is used for the determination of ee, an accuracy of only >96% is claimed.
21. Chen, C.-S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294.
22. Boldrini, G. P.; Lodi, L.; Tagliavini, E.; Trombini, C.; Umani-Rochini, A. J. Organomet. Chem. 1987, 336, 23.