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通过不对称氢化实现氟甲基化立体中心的催化对映选择性合成。

Catalytic enantioselective synthesis of fluoromethylated stereocenters by asymmetric hydrogenation.

作者信息

Yang Jianping, Ponra Sudipta, Li Xingzhen, Peters Bram B C, Massaro Luca, Zhou Taigang, Andersson Pher G

机构信息

Department of Organic Chemistry, Stockholm University, Arrhenius Laboratory 106 91 Stockholm Sweden

College of Chemistry and Chemical Engineering, Southwest Petroleum University Chengdu Sichuan 610500 China

出版信息

Chem Sci. 2022 Jun 29;13(29):8590-8596. doi: 10.1039/d2sc02685f. eCollection 2022 Jul 29.

Abstract

Fluoromethyl groups possess specific steric and electronic properties and serve as a bioisostere of alcohol, thiol, nitro, and other functional groups, which are important in an assortment of molecular recognition processes. Herein we report a catalytic method for the asymmetric synthesis of a variety of enantioenriched products bearing fluoromethylated stereocenters with excellent yields and enantioselectivities. Various N,P-ligands were designed and applied in the hydrogenation of fluoromethylated olefins and vinyl fluorides.

摘要

氟甲基具有特定的空间和电子性质,可作为醇、硫醇、硝基及其他官能团的生物电子等排体,这些官能团在各种分子识别过程中很重要。在此,我们报道了一种催化方法,用于不对称合成多种带有氟甲基化立体中心的对映体富集产物,产率和对映选择性优异。设计了各种N,P-配体并将其应用于氟甲基化烯烃和氟乙烯的氢化反应中。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ddac/9337738/cb8d8d2a8826/d2sc02685f-f1.jpg

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