On the use of succinic anhydride as acylating agent for practical resolution of aryl-alkyl alcohols through lipase-catalyzed acylation

被引：46

作者：

Bouzemi, N

Debbeche, H

Aribi-Zouioueche, L

Fiaud, JC ^{[1
]}

机构：

[1] Univ Paris 11, Lab Catalyse Mol, F-91405 Orsay, France

[2] Univ Annaba, Grp Synth Asymetr & Biocatalyse, Annaba 23000, Algeria

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 03期

关键词：

alkyl-aryl secondary alcohols; acylation; Candida antartica lipase B (CAL B); Pseudomonas fluorescens lipase (PFL); succinic anhydride;

D O I：

10.1016/j.tetlet.2003.10.208

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A comparison is carried out of the E-values recorded in the lipase-catalyzed resolution of a series of secondary aryl-alkyl alcohols with enol esters versus succinic anhydride. Whereas all the substrates could be resolved by a proper choice of the lipase/enol ester couple with moderate (E = 50) to good (E > 100) enantioselectivities, only some of them showed satisfactory enantioselectivity (E > 50) with the use of succinic acid as acylating agent. Notably, indanol and 1-quinolin-3-yl-ethanol were resolved in a practical way, with E > 100 and E > 80, respectively. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：627 / 630

页数：4

共 22 条

[1] Resolution of derivatives of 1,2-propanediol with lipase B from Candida antarctica -: Effect of substrate structure, medium, water activity and acyl donor on enantiomeric ratio [J].