Enantioselective Construction of Axially Chiral Amino Sulfide Vinyl Arenes by Chiral Sulfide‐Catalyzed Electrophilic Carbothiolation of Alkynes
Yaoyu Liang, Jieying Ji, Xiaoyan Zhang, Quanbin Jiang, Jie Luo, Xiaodan Zhao
Abstract
The enantioselective construction of axially chiral compounds by electrophilic carbothiolation of alkynes is disclosed for the first time. This enantioselective transformation is enabled by the use of a Ts-protected bifunctional sulfide catalyst and Ms-protected ortho-alkynylaryl amines (Ts=tosyl; Ms=mesyl). Both electrophilic arylthiolating and electrophilic trifluoromethylthiolating reagents are suitable for this reaction. The obtained products of axially chiral vinyl-aryl amino sulfides can be easily converted into biaryl amino sulfides, biaryl amino sulfoxides, biaryl amines, vinyl-aryl amines, and other valuable difunctionalized compounds.
Topics & Concepts
Enantioselective synthesisElectrophileSulfideChemistryArylCatalysisBifunctionalOrganic chemistryCombinatorial chemistryReagentElectrophilic aminationAminationAlkylAxial and Atropisomeric Chirality SynthesisSphingolipid Metabolism and SignalingCatalytic C–H Functionalization Methods