Lipase-catalyzed kinetic resolution of Baylis-Hillman products

Tetrahedron Asymmetry

Volumn 9, Issue 21, 1998, Pages 3825-3830

  Hayashi, Nobuyuki ^a   Yanagihara, Kazuhito ^a   Tsuboi, Sadao ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3 ACETOXY 2 METHYLENEPENTANOATE; 3 HYDROXY 2 METHYLENEBUTANOATE; 3 HYDROXY 2 METHYLENEPENTANOATE; ACETIC ACID DERIVATIVE; ACETONITRILE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; ENANTIOMER; ENZYME KINETICS; ESTERIFICATION; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; RACEMIC MIXTURE;

EID: 0032491526     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00405-4     Document Type: Article

References (13)

1. (a) Baylis, A. B.; Hillman, M. E. D. German Patent 2,155,113. Chem. Abstr. 1972, 77, 34,174q. However, a similar reaction had been reported as a patent in 1967 by Japanese scientists,
2. (b) Toyo Rayon Co., Ltd. French Patent 1,506,132. Chem. Abstr. 1969, 70, 19613u.
3. (c) Morita, K.; Suzuki, Z.; Hirose, H. Bull. Chem. Soc. Jpn. 1968, 41, 2815.
4. Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001 and references cited therein.
5. (a) Burgess, K., Jennings, L. D. J. Org. Chem. 1990, 55, 1138.
6. (b) Basavaiah, D.; Dharma Rao, P. Synth. Commun. 1994, 24, 917.
7. (c) Adam, W.; Hoch, U.; Saha-Moller, C. R.; Schreier, P. Angew. Chem., Int. Ed. Engl. 1993, 32, 1737.
8. Compound (±)-5a in Table 1: Culvenor, C. C.; Geissman, T. A. J. Am. Chem. Soc. 1961, 83, 1647.
9. The absolute configurations of the optically active compounds were assumed from the specific rotations by comparison with those of the similar compounds cited above in Ref. 3a.
10. Oohashi, K.; Ido, S. Jpn. Kokai Tokkyo Koho JP 05 17,375. Chem. Abstr. 1993, 118, 254,552s.
11. The enantiomers of the alcohols were perfectly separated on the chiral column. On the other hand, those of acetates did not separate at all, except for 4a. Accordingly, the enantiomeric purities of the inseparable acetates were determined after hydrolyzing to the corresponding alcohols with aq. 19% HCl in acetone.
12. p represent the enantiomeric excesses of substrate and product, respectively. See Chen, C. S.; Fujimoto, K.; Girdaukas, K.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294.
13. McFadden, H. G.; Harris, R. L. N.; Jenkins, C. L. D. Aust. J. Chem. 1989, 42, 301.