Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters from dialkyl 2-oxoglutarates

被引：21

作者：

Drioli, S ^{[1
]}

Nitti, P ^{[1
]}

Pitacco, G ^{[1
]}

Tossut, L ^{[1
]}

Valentin, E ^{[1
]}

机构：

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

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 14期

关键词：

D O I：

10.1016/S0957-4166(99)00286-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters can be prepared either by enzymatic resolution of the racemic gamma-lactones themselves or by bioreduction with baker's yeast of dialkyl 2-oxoglutarates and subsequent cyclization of the resulting dialkyl 2-hydroxyglutarates. The best results were obtained by the former route, by which the desired compounds were isolated in high enantiomeric excess. Bioreductions were less satisfactory. In fact the hydroxyester intermediates were initially formed as racemic mixtures and their final enantiomeric enrichment was reached by asymmetric destruction, occurring in the bioreaction medium, however at the same time large amounts of alkyl 4-hydroxybutanoates were formed as side products. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2713 / 2728

页数：16

共 68 条

[51] SYNTHESE IN 4-STELLUNG CARBATHOXY-SUBSTITUIERTER CYCLOHEXENONE [J].