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Copper‐Catalyzed Enantioselective Trifluoromethoxylation of Propargyl Sulfonates

Yangdong Hou, Zhang Zhang, Xinyu Sun, Zheng Yang, Yu‐Xin Luan, Pingping Tang

2023Angewandte Chemie International Edition34 citationsDOI

Abstract

Abstract Due to the strong electron‐withdrawing nature and high lipophilicity of trifluoromethoxy group (OCF 3 ), methods for introducing OCF 3 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.

Topics & Concepts

Enantioselective synthesisPropargylTrifluoromethylLipophilicityCatalysisChemistryCopperOrganic chemistryCombinatorial chemistryAlkylFluorine in Organic ChemistryCyclopropane Reaction Mechanisms
Copper‐Catalyzed Enantioselective Trifluoromethoxylation of Propargyl Sulfonates | Litcius