通过生物催化动态还原动力学拆分实现手性 α-取代-β-羟基芳基膦酸酯的获得。

Access to chiral α-substituted-β-hydroxy arylphosphonates enabled by biocatalytic dynamic reductive kinetic resolution.

机构信息

Department of Chemistry, Engineering Center of Catalysis and Synthesis for Chiral Molecules, Fudan University, Shanghai Engineering Research Center of Industrial Asymmetric Catalysis of Chiral Drugs, 220 Handan Road, Shanghai, 200433, P. R. China.

FAFU-UCR Joint Center for Horticultural Biology and Metabolomics, Fujian Provincial Key Laboratory of Haixia Applied Plant Systems Biology, Fujian Agriculture and Forestry University, Fuzhou, 350002, P. R. China.

出版信息

Org Biomol Chem. 2020 Apr 8;18(14):2672-2677. doi: 10.1039/d0ob00379d.

DOI:10.1039/d0ob00379d

PMID:32202289

Abstract

Ketoreductase (KRED)-catalyzed dynamic reductive kinetic resolution (DYRKR) of α-substituted-β-keto arylphosphonates was developed as a generic and stereoselective approach to synthesize chiral α-substituted-β-hydroxy arylphosphonates, with moderate-to-excellent isolated yield (up to 96%), good-to-excellent diastereoselectivity (up to >99 : <1 dr), and excellent enantioselectivity (up to >99% ee) being achieved.

摘要

酮还原酶 (KRED) 催化的 α-取代-β-酮芳基膦酸酯的动态还原动力学拆分 (DYRKR) 已被开发为一种通用且对映选择性的方法，用于合成手性的 α-取代-β-羟基芳基膦酸酯，具有中等至优异的分离收率（高达 96%）、良好至优异的非对映选择性（高达 >99:1 dr）和优异的对映选择性（高达 >99%ee）。