Enantioselective monoreduction of different 1,2-diaryl-1,2-diketones catalysed by lyophilised whole cells from Pichia glucozyma

被引：37

作者：

Hoyos, Pilar ^{[1
]}

Sansottera, Giacomo ^{[2
]}

Fernandez, Maria ^{[1
]}

Molinari, Francesco ^{[2
]}

Vicente Sinisterra, Jose ^{[1
,3
]}

Alcantara, Andres R. ^{[1
,3
]}

机构：

[1] Univ Complutense Madrid, Fac Farm, Dept Quim Organ & Farmaceut, Grp Biotransformac, E-28040 Madrid, Spain

[2] Univ Milan, Dipartimento Sci & Tecnol Alimentari & Microbiol, I-20133 Milan, Italy

[3] PTM, Parque Cient Madrid, Unidad Biotransformac Ind, Madrid 28760, Spain

来源：

TETRAHEDRON | 2008年 / 64卷 / 34期

关键词：

alpha-diketones; benzoins; stereoselective reductions;

D O I：

10.1016/j.tet.2008.06.019

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this work we have studied the monoreduction of different 1,2-diaryl-ethanediones (benzils, 1) with lyophilised whole cells from Pichia glucozyma CBS 5766, using the diphenyl compound (benzil, 1a) as model substrate, and extended the enantioselective reduction to structurally different symmetric benzils for producing enantiomerically pure or enriched benzoins (alpha-hydroxyketones 2) in high yields and very short reaction times. In order to study the regio- and stereoselectivity of this biocatalyst, we examined the reduction of diaryldiketones formed from different aryl moieties, to obtain symmetric and asymmetric crossed-benzoins. This methodology is conducted under very mild reaction conditions (aqueous media with small amounts of DMSO for solubilising the substrates, T=28 degrees C), therefore constituting a green alternative compared to other reported procedures for obtaining homochiral benzoins. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：7929 / 7936

页数：8

共 47 条

[31] Mechanism for improving stereoselectivity for asymmetric reduction using acetone powder of microorganism [J].