The influence of microwave irradiation on lipase-catalyzed kinetic resolution of racemic secondary alcohols

被引：34
作者：
Bachu, Prabhakar [1 ]
Gibson, Jennifer S. [1 ]
Sperry, Jonathan [1 ]
Brimble, Margaret A. [1 ]
机构：
[1] Univ Auckland, Dept Chem, Auckland, New Zealand
来源：
TETRAHEDRON-ASYMMETRY | 2007年 / 18卷 / 13期
关键词：
ENANTIOSELECTIVE TOTAL-SYNTHESIS; ORGANIC-SYNTHESIS; IONIC LIQUIDS; ENHANCED ENANTIOSELECTIVITY; ENZYMATIC RESOLUTION; SYNTHETIC ROUTE; TRANSESTERIFICATION; BIOCATALYSIS; INHIBITOR; CONSTRUCTION;
D O I：
10.1016/j.tetasy.2007.06.035
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The influence of microwave irradiation on the Novozyme 4350 (Candida antarctica lipase) catalyzed kinetic resolution of secondary alcohols with different functional groups was studied in comparison to the use of conventional heating at 60 degrees C. p-Chlorophenyl acetate was used as an acyl donor and toluene as the solvent. (+/-)-1-Phenyl-1-propanol 1, (+/-)-1-(4-bromophenyl)-propan-1-ol 3, (+/-)-1-phenylbut-3-en-1-ol 5 and (+/-)-3-bromo-2-(2-hydroxypropyl)-1,4-dimethoxynaphthalene 7 were successfully resolved into their (S)-alcohols and (R)-esters, respectively, in good enantiomeric excess. Resolution of (+/-)-ethyl-5-(4-methoxybenyloxy)-3-hydroxypentanoate 9 afforded its (R)-alcohol and (S)-ester using this method. In addition, microwave-assisted lipase transesterification of meso-symmetric diol 11 effected desymmetrization to ester 12 with high enantiomeric excess. In all cases studied, the conversion value for the microwave-assisted lipase kinetic resolution of secondary alcohols was higher than that obtained using conventional heating. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1618 / 1624
页数：7
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