Biocatalyzed Enantioselective Reduction of Activated C=C Bonds: Synthesis of Enantiomerically Enriched α-Halo-β-arylpropionic Acids

被引：29

作者：

Brenna, Elisabetta ^{[1
]}

Gatti, Francesco G. ^{[1
]}

Manfredi, Alessia ^{[1
]}

Monti, Daniela ^{[2
]}

Parmeggiani, Fabio ^{[1
]}

机构：

[1] Politecn Milan, Dipartimento Chim, I-20131 Milan, Italy

[2] CNR, Ist Chim Riconoscimento Mol, I-20131 Milan, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 20-21期

关键词：

Enzyme catalysis; Biocatalysis; Reduction; Asymmetric synthesis; Biotransformations; OLD YELLOW ENZYME; AMINO-ACIDS; ASYMMETRIC HYDROGENATION; FAMILY; YEAST; EFFICIENT; DERIVATIVES; INHIBITORS; RESOLUTION; DISCOVERY;

D O I：

10.1002/ejoc.201100537

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective biocatalyzed reduction of the C=C bond of some (Z)-methyl alpha-halo-beta-arylacrylates was investigated. The reaction was performed by baker's yeast fermentation and Old Yellow Enzymes 1-3 mediated biotransformations. The final products were, respectively, enantiomerically enriched (S)-alpha-halo-beta-arylpropionic acids and their methyl esters, and ester hydrolysis was promoted in the whole cell system. High conversions and enantioselectivity values were observed when the aromatic ring was substituted by an electron-withdrawing group. Further manipulation of two of these enantiomerically enriched (S)-haloacids afforded p-substituted D-phenylalanines.

引用

页码：4015 / 4022

页数：8

共 77 条

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