Catalytic enantioselective synthesis of fluoromethylated stereocenters by asymmetric hydrogenation

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

doi:10.1039/d2sc02685f

Catalytic enantioselective synthesis of fluoromethylated stereocenters by asymmetric hydrogenation

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

Authors

Jianping Yang¹, Sudipta Ponra¹, Xingzhen Li², Bram B C Peters¹, Luca Massaro¹, Taigang Zhou², Pher G Andersson^{1

3}

Affiliations

¹ Department of Organic Chemistry, Stockholm University, Arrhenius Laboratory 106 91 Stockholm Sweden pher.andersson@su.se.
² College of Chemistry and Chemical Engineering, Southwest Petroleum University Chengdu Sichuan 610500 China tgzhou@swpu.edu.cn.
³ School of Chemistry and Physics, University of Kwazulu-Natal Private Bag X54001 Durban 4000 South Africa.

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.