Lipase-catalyzed transesterification of 2-phenyl-1-propanol with vinyl esters having aromatic ring in acyl moiety

被引:29
作者
Kawasaki, M
Goto, M
Kawabata, S
Kodama, T
Kometani, T
机构
[1] Toyama Prefectural Univ, Fac Engn, Toyama 9390398, Japan
[2] Toyama Natl Coll Technol, Toyama 9398630, Japan
关键词
enantioselection; enzymes and enzyme reactions; resolution;
D O I
10.1016/S0040-4039(99)00943-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The highly enantioselective transesterification of 2-phenyl-1-propanol, which has not been efficiently resolved by lipase-catalyzed reactions, was attained by using either vinyl 3-(p-tolyl)propanoate or vinyl 3-(2-naphthyl)propanoate as the acyl donor. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5223 / 5226
页数:4
相关论文
共 25 条
[11]   Microwave-promoted lipase-catalyzed reactions [J].
Lin, GL ;
Lin, WY .
TETRAHEDRON LETTERS, 1998, 39 (24) :4333-4336
[12]  
LOBELL M, 1994, SYNTHESIS-STUTTGART, P375
[13]  
MATSUMOTO T, 1994, CHEM PHARM BULL, V42, P1191
[14]   Resolution of 2-phenoxy-1-propanols by Pseudomonas sp. lipase-catalyzed highly enantioselective transesterification:: influence of reaction conditions on the enantioselectivity toward primary alcohols [J].
Miyazawa, T ;
Yukawa, T ;
Ueji, S ;
Yanagihara, R ;
Yamada, T .
BIOTECHNOLOGY LETTERS, 1998, 20 (03) :235-238
[15]   RESOLUTION OF MANDELIC-ACIDS BY LIPASE-CATALYZED TRANSESTERIFICATIONS IN ORGANIC MEDIA - INVERSION OF ENANTIOSELECTIVITY MEDIATED BY THE ACYL DONOR [J].
MIYAZAWA, T ;
KURITA, S ;
UEJI, S ;
YAMADA, T ;
KUWATA, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (18) :2253-2255
[16]   Lipase-catalyzed kinetic resolution of 3-butyn-2-ol [J].
Nakamura, K ;
Takenaka, K ;
Ohno, A .
TETRAHEDRON-ASYMMETRY, 1998, 9 (24) :4429-4439
[17]   Enzymatic resolution of alicyclic 1,3-amino alcohols in organic media [J].
Péter, M ;
Van der Eycken, J ;
Bernáth, G ;
Fülöp, F .
TETRAHEDRON-ASYMMETRY, 1998, 9 (13) :2339-2347
[18]   Enhancement of the enantioselectivity in lipase-catalyzed kinetic resolutions of 3-phenyl-2H-azirine-2-methanol by lowering the temperature to -40 degrees C [J].
Sakai, T ;
Kawabata, I ;
Kishimoto, T ;
Ema, T ;
Utaka, M .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (15) :4906-4907
[19]   Low-temperature method for enhancement of enantioselectivity in the lipase-catalyzed kinetic resolutions of solketal and some chiral alcohols [J].
Sakai, T ;
Kishimoto, T ;
Tanaka, Y ;
Ema, T ;
Utaka, M .
TETRAHEDRON LETTERS, 1998, 39 (43) :7881-7884
[20]   LIPASE-CATALYZED TRANSESTERIFICATION IN ORGANIC-SOLVENTS - APPLICATIONS TO THE PREPARATION OF ENANTIOMERICALLY PURE COMPOUNDS [J].
SANTANIELLO, E ;
FERRABOSCHI, P ;
GRISENTI, P .
ENZYME AND MICROBIAL TECHNOLOGY, 1993, 15 (05) :367-382