SYNTHESIS OF 2,4-DIMETHYLGLUTARIC ACID MONOESTERS VIA ENZYME-CATALYZED ASYMMETRIC ALCOHOLYSIS OF MESO-2,4-DIMETHYLGLUTARIC ANHYDRIDE

被引:25
作者
OZEGOWSKI, R
KUNATH, A
SCHICK, H
机构
[1] Centre of Selective Organic Synthesis, D(O)- 1199 Berlin-Adlershof
关键词
D O I
10.1016/S0957-4166(00)80177-9
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
1-(2-Methylpropyl) 5-hydrogen (2R,4S)2,4-dimethylpentanedioate with an enantiomeric excess of 90 % was obtained in a yield of 72 % from meso-2,4-dimethylpentanedioic anhydride and 2-methylpropanol by an asymmetric alcoholysis catalyzed by the lipase from Candida sp. 382.
引用
收藏
页码:695 / 698
页数:4
相关论文
共 20 条
[1]   HIGHLY STEREOSELECTIVE SYNTHESIS OF (+/-)-ALPHA-MULTISTRIATIN [J].
BARTLETT, PA ;
MYERSON, J .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (10) :1625-1627
[2]  
Chen C.-S., 1989, ANGEW CHEM, V101, P711
[3]   BIFUNCTIONAL CHIRAL SYNTHONS VIA MICROBIOLOGICAL METHODS .1. OPTICALLY-ACTIVE 2,4-DIMETHYLGLUTARIC ACID MONOMETHYL ESTERS [J].
CHEN, CS ;
FUJIMOTO, Y ;
SIH, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (12) :3580-3582
[4]   GENERAL-ASPECTS AND OPTIMIZATION OF ENANTIOSELECTIVE BIOCATALYSIS IN ORGANIC-SOLVENTS - THE USE OF LIPASES [J].
CHEN, CS ;
SIH, CJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (06) :695-707
[5]   AN EFFICIENT ROUTE TO TRIENE SYNTHONS FOR PUTATIVE INTERMEDIATES IN POLYETHER ANTIBIOTIC BIOSYNTHESIS [J].
DYER, UC ;
ROBINSON, JA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (01) :53-60
[6]  
HENKEL B, IN PRESS TETRAHEDRON
[7]   ENANTIOTOPIC-GROUP DIFFERENTIATION - CATALYTIC ASYMMETRIC RING-OPENING OF PROCHIRAL CYCLIC ACID ANHYDRIDES WITH METHANOL, USING CINCHONA ALKALOIDS [J].
HIRATAKE, J ;
INAGAKI, M ;
YAMAMOTO, Y ;
ODA, J .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (05) :1053-1058
[8]   STEREOSELECTIVE SYNTHESIS OF ALCOHOLS .11. DOUBLE STEREODIFFERENTIATION IN THE ADDITION OF CROTYLBORONATES TO ALDEHYDES - PRELOG-DJERASSI LACTONE [J].
HOFFMANN, RW ;
ZEISS, HJ ;
LADNER, W ;
TABCHE, S .
CHEMISCHE BERICHTE-RECUEIL, 1982, 115 (06) :2357-2370
[9]   PREPARATION OF USEFUL CHIRAL LACTONE SYNTHONS VIA STEREOSPECIFIC ENZYME-CATALYZED OXIDATIONS OF MESO-DIOLS [J].
JAKOVAC, IJ ;
NG, G ;
LOK, KP ;
JONES, JB .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (11) :515-516
[10]   ASYMMETRIC TRANSFORMATIONS CATALYZED BY ENZYMES IN ORGANIC-SOLVENTS [J].
KLIBANOV, AM .
ACCOUNTS OF CHEMICAL RESEARCH, 1990, 23 (04) :114-120