TRANSESTERIFICATION-BASED ENZYMATIC RESOLUTIONS OF RACEMIC 3-HYDROXY-4-PENTENYLURETHANES IN ORGANIC-SOLVENTS

被引:17
作者
TAKAHATA, H
UCHIDA, Y
MOMOSE, T
机构
[1] Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, Toyama, 930-01
关键词
TRANSESTERIFICATION; IMMOBILIZED LIPASE; 3-HYDROXY-4-PENTENYLURETHANE; CHIRON;
D O I
10.1016/S0040-4039(00)92080-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An expedient synthesis of homochiral N-protected (R)- and (S)-3-hydroxy-4-pentenylamines (1 and 2) has been accomplished Wa the enzymatic resolution of the racemic 1 and 2 mediated by immobilized lipase in pentane.
引用
收藏
页码:3331 / 3332
页数:2
相关论文
共 10 条
[1]   ANHYDRIDES AS ACYLATING AGENTS IN LIPASE-CATALYZED STEREOSELECTIVE ESTERIFICATION OF RACEMIC ALCOHOLS [J].
BIANCHI, D ;
CESTI, P ;
BATTISTEL, E .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (23) :5531-5534
[2]   ENANTIOSELECTIVE ESTERIFICATIONS OF UNSATURATED ALCOHOLS MEDIATED BY A LIPASE PREPARED FROM PSEUDOMONAS SP [J].
BURGESS, K ;
JENNINGS, LD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (16) :6129-6139
[3]   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
[4]   ENZYMATIC-REACTIONS IN ORGANIC-SYNTHESIS .2. ESTER INTERCHANGE OF VINYL ESTERS [J].
DEGUEILCASTAING, M ;
DEJESO, B ;
DROUILLARD, S ;
MAILLARD, B .
TETRAHEDRON LETTERS, 1987, 28 (09) :953-954
[5]   CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION [J].
GAO, Y ;
HANSON, RM ;
KLUNDER, JM ;
KO, SY ;
MASAMUNE, H ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) :5765-5780
[6]   ASYMMETRIC TRANSFORMATIONS CATALYZED BY ENZYMES IN ORGANIC-SOLVENTS [J].
KLIBANOV, AM .
ACCOUNTS OF CHEMICAL RESEARCH, 1990, 23 (04) :114-120
[7]   THE SHORTEST SYNTHESIS OF OPTICALLY-ACTIVE GEISSMAN-WAISS LACTONE, A KEY SYNTHETIC INTERMEDIATE FOR NECINE BASES [J].
TAKAHATA, H ;
BANBA, Y ;
MOMOSE, T .
TETRAHEDRON-ASYMMETRY, 1991, 2 (06) :445-448
[8]   AN ASYMMETRIC TOTAL SYNTHESIS OF (-)-SUPINIDINE [J].
TAKAHATA, H ;
BANBA, Y ;
MOMOSE, T .
TETRAHEDRON, 1991, 47 (36) :7635-7644
[9]   ASYMMETRIC INTRAMOLECULAR AMIDATION OF N-(TERT-BUTOXYCARBONYL)-3-HYDROXY-4-PENTENYLAMINE - A NEW ENTRY TO CHIRAL BUILDING-BLOCKS FOR THE SYNTHESIS OF BIOLOGICALLY-ACTIVE NITROGEN-CONTAINING COMPOUNDS [J].
TAKAHATA, H ;
BANBA, Y ;
TAJIMA, M ;
MOMOSE, T .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (01) :240-245
[10]   ASYMMETRIC-SYNTHESIS OF 1-HYDROXYINDOLIZIDINES, BIOSYNTHETIC PRECURSORS TO THE TOXIC INDOLIZIDINE ALKALOIDS SLAFRAMINE AND SWAINSONINE [J].
TAKAHATA, H ;
BANBA, Y ;
MOMOSE, T .
TETRAHEDRON-ASYMMETRY, 1990, 1 (11) :763-764