Copper-Catalyzed Enantioselective Trifluoromethoxylation of Propargyl Sulfonates

Angew Chem Int Ed Engl. 2023 Apr 24;62(18):e202218919. doi: 10.1002/anie.202218919. Epub 2023 Mar 27.

Abstract

Due to the strong electron-withdrawing nature and high lipophilicity of trifluoromethoxy group (OCF3 ), methods for introducing OCF3 into organic molecules are in high demand. However, the research area of direct enantioselective trifluoromethoxylation is still in the embryonic stage, with limited enantioselectivity and/or reaction types. Here, we describe the first copper-catalyzed enantioselective trifluoromethoxylation of propargyl sulfonates using trifluoromethyl arylsulfonate (TFMS) as the trifluoromethoxy source in up to 96 % ee.

Keywords: Copper; Enantioselective; Propargyl; Sulfonates; Trifluoromethoxylation.