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Asymmetric Synthesis of Biaryl Sulfilimines Bearing Multiple Chiral Elements Involving Cyclic Diaryliodoniums

Xiangyu Liu, Zenghui Ye, Jici Liu, Yanqi Wu, Fengzhi Zhang

2025Organic Letters14 citationsDOI

Abstract

The enantio- and diastereoselective synthesis of biaryl atropisomers with a sulfur stereogenic center is a significant challenge for current chemical synthesis due to the lack of effective synthetic strategies. Herein, we report an efficient method for the construction of chiral biaryl sulfilimines possessing both axial and sulfur central chiralities via copper/chiral cobalt anion-catalyzed sulfuration of cyclic diaryliodoniums under mild conditions. Various axial chiral biaryl sulfilimines were efficiently prepared in high yields (up to 99%) and enantioselectivities (up to 98% ee), which can be easily transformed into a wide range of valuable chiral biaryl sulfoximines and their derivatives.

Topics & Concepts

ChemistryBearing (navigation)StereochemistryCombinatorial chemistryComputational chemistryComputer scienceArtificial intelligenceSynthesis and Catalytic ReactionsAxial and Atropisomeric Chirality SynthesisCatalytic C–H Functionalization Methods
Asymmetric Synthesis of Biaryl Sulfilimines Bearing Multiple Chiral Elements Involving Cyclic Diaryliodoniums | Litcius