Enzymatic resolution of 1,1-dimethoxybut-3-en-2-ol and 1,1-dimethoxypent-4-en-2-ol, α-hydroxyaldehyde precursors for aldol-type reactions

被引：11

作者：

Chênevert, R

Gravil, S

Bolte, J

机构：

[1] Univ Laval, Fac Sci & Genie, CREFSIP, Dept Chim, Quebec City, PQ G1K 7P4, Canada

[2] Univ Clermont Ferrand, UMR 6504 CNRS, Lab Synth & Etud Syst Interet Biol, F-63177 Aubiere, France

来源：

TETRAHEDRON-ASYMMETRY | 2005年 / 16卷 / 12期

基金：

加拿大自然科学与工程研究理事会;

关键词：

D O I：

10.1016/j.tetasy.2005.05.013

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Hydroxyacetals 2 and 3 were resolved by acylation with vinyl acetate in the presence of lipases in organic media. The reverse reaction, the enzymatic hydrolysis of the corresponding acetates, was also highly stereoselective and provided the opposite enantiomers. (c) 2005 Elsevier Ltd. All rights reserved.

引用

收藏

页码：2081 / 2086

页数：6

相关论文

共 47 条

[1] Advances in asymmetric enolate methodology [J].

Arya, P ;

Qin, HP .

TETRAHEDRON, 2000, 56 (07) :917-947

[2] Acylnitrene route to vicinal amino alcohols. Application to the synthesis of (-)-bestatin and analogues [J].

Bergmeier, SC ;

Stanchina, DM .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (08) :2852-2859

[3] Enantioselectivities of yeast epoxide hydrolases for 1,2-epoxides [J].

Botes, AL ;

Weijers, CAGM ;

Botes, PJ ;

van Dyk, MS .

TETRAHEDRON-ASYMMETRY, 1999, 10 (17) :3327-3336

[4] Carbon-carbon coupling in biotransformation [J].

Breuer, M ;

Hauer, B .

CURRENT OPINION IN BIOTECHNOLOGY, 2003, 14 (06) :570-576

[5] 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

[6] THERMALLY INDUCED REARRANGEMENTS OF 2-VINYLOXIRANE [J].

CRAWFORD, RJ ;

LUTENER, SB ;

COCKCROFT, RD .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1976, 54 (21) :3364-3376

[7] Transketolase and fructose-1,6-bis-phosphate aldolase, complementary tools for access to new ulosonic acid analogues [J].

Crestia, D ;

Demuynck, C ;

Bolte, J .

TETRAHEDRON, 2004, 60 (10) :2417-2425

[8] The asymmetric hetero-Diels-Alder reaction and addition of allylic organometallics to 10-N,N-dicyclohexylsulphamoyl(2R)-isobornyl glyoxylate [J].

Czapla, A ;

Chajewski, A ;

Kiegiel, K ;

Bauer, T ;

Wielogorski, Z ;

Urbanczyk-Lipkowska, Z ;

Jurczak, J .

TETRAHEDRON-ASYMMETRY, 1999, 10 (11) :2101-2111

[9] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

[10] A chemoenzymatic approach to the synthesis of the stereoisomers of a β-adrenergic receptor antagonist [J].

Dallanoce, C ;

De Amici, M ;

Carrea, G ;

Secundo, F ;

Castellano, S ;

De Micheli, C .

TETRAHEDRON-ASYMMETRY, 2000, 11 (13) :2741-2751

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