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
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
收藏
页码:617 / 625
页数:9
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