Lipase-catalyzed kinetic resolution of racemic seven-membered substituted lactones

被引:17
作者
Shioji, K [1 ]
Matsuo, A
Okuma, K
Nakamura, K
Ohno, A
机构
[1] Fukuoka Univ, Fac Sci, Dept Chem, Jonan ku, Fukuoka 8140180, Japan
[2] Kyoto Univ, Inst Chem Res, Kyoto 6110011, Japan
关键词
enzymes and enzyme reaction; hydrolysis; lactone;
D O I
10.1016/S0040-4039(00)01421-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Optically active 3-, 4-, 5-, or 6-methyl substituted seven-membered lactones were prepared by Candida antarctica lipase (CAL)-catalyzed kinetic resolution of the racemic lactones. Among these lactones, only in the case of 5-methylhexanolide (R)-isomer reacts faster than the other enantiomer, while the rest of lactones show (S)-selectivity. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8799 / 8802
页数:4
相关论文
共 6 条
[1]   ENZYMATIC RESOLUTION OF RACEMIC LACTONES [J].
BLANCO, L ;
GUIBEJAMPEL, E ;
ROUSSEAU, G .
TETRAHEDRON LETTERS, 1988, 29 (16) :1915-1918
[2]   RESOLUTION OF RACEMIC EPSILON-LACTONES [J].
FELLOUS, R ;
LIZZANICUVELIER, L ;
LOISEAU, MA ;
SASSY, E .
TETRAHEDRON-ASYMMETRY, 1994, 5 (03) :343-346
[3]  
Kayser M, 1999, SYNLETT, P153
[4]   Chemoenzymatic autocatalytic Baeyer-Villiger oxidation [J].
Pchelka, BK ;
Gelo-Pujic, M ;
Guibe-Jampel, E .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (17) :2625-2627
[5]   Recombinant baker's yeast as a whole-cell catalyst for asymmetric Baeyer-Villiger oxidations [J].
Stewart, JD ;
Reed, KW ;
Martinez, CA ;
Zhu, J ;
Chen, G ;
Kayser, MM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (15) :3541-3548
[6]   LIPASE-SUPPORTED SYNTHESIS OF BIOLOGICALLY-ACTIVE COMPOUNDS [J].
THEIL, F .
CHEMICAL REVIEWS, 1995, 95 (06) :2203-2227