Regioselective Ring-Opening of Styrene Oxide Derivatives Using Halohydrin Dehalogenase for Synthesis of 4-Aryloxazolidinones

被引：29

作者：

Wan, Nanwei ^{[1
]}

Tian, Jiawei ^{[1
]}

Zhou, Xiaoying ^{[1
]}

Wang, Huihui ^{[1
]}

Cui, Baodong ^{[1
]}

Han, Wenyong ^{[1
]}

Chen, Yongzheng ^{[1
]}

机构：

[1] Zunyi Med Univ, Green Pharmaceut Engn Res Ctr Guizhou Prov, Sch Pharm, Gener Drug Res Ctr Guizhou Prov,Key Lab Biocataly, Zunyi 563000, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2019年 / 361卷 / 20期

基金：

中国国家自然科学基金;

关键词：

Oxazolidinones; Halohydrin dehalogenase; Epoxides; Regioselectivity; Ring-opening; EFFICIENT SYNTHESIS; CATALYZED SYNTHESIS; BIOLOGICAL-ACTIVITY; OXAZOLIDINONES; BIOCATALYSIS; EPOXIDES;

D O I：

10.1002/adsc.201900786

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A biocatalytic approach towards a range of 4-aryloxazolidinones is developed using a halohydrin dehalogenase from Ilumatobacter coccineus (HheG) as biocatalyst. The method is based on the HheG-catalyzed alpha-position regioselective ring-opening of styrene oxide derivatives with cyanate as a nucleophile, producing the corresponding 4-aryloxazolidinones in moderate to good yields. Synthesis of enantiopure 4-aryloxazolidinones is also achievable using chiral epoxide materials.

引用

页码：4651 / 4655

页数：5

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