Chemoenzymatic synthesis of enantioenriched 5-oxo-tetrahydro-3-furancarboxylic acid derivatives

被引：26

作者：

Comini, A ^{[1
]}

Forzato, C ^{[1
]}

Nitti, P ^{[1
]}

Pitacco, G ^{[1
]}

Valentin, E ^{[1
]}

机构：

[1] Univ Trieste, Dipartimento Sci Chim, I-34127 Trieste, Italy

来源：

TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 04期

关键词：

lactones; enzymatic resolution; baker's yeast; circular dichroism; paraconic acids;

D O I：

10.1016/j.tetasy.2004.01.001

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

(R)-(+)-Paraconic acid 4, (S)-(-)-terebic acid 6 and their corresponding methyl and ethyl esters having ee's ranging from 60% to 92% were obtained by enzymatic resolution of their racemates. The enzymatic resolution of racemic ethyl gamma-methylparaconates 14a and 14b allowed the isolation of the unreacted ester (2R,3R)-(+)-14a and that of the lactonic acid (2S,3R)-(-)-5b with 80% and 93% ee, respectively, the former by the use of Horse liver acetone powder (HLAP), the latter using alpha-chymotrypsin (alpha-CT). The enantiomeric ethyl (2S,3S)-(-)-14a and (2S,3R)-(-)-14b, both with >99% ee, were obtained by baker's yeast reduction of diethyl acetylsuccinate. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：617 / 625

页数：9

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