Enantioselective sulfinylation of alcohols and amines by condensation with sulfinates

Abstract

Achieving the preparation of enantiomerically enriched S-stereogenic compounds is a long-standing objective in stereoselective synthesis, owing to the fundamental importance and broad applications of these chiral scaffolds in various fields. Despite recent significant advancements, catalyst-controlled stereoselective synthesis of S-stereogenic compounds remains to be a considerable challenge, particularly by means of small-molecule catalysts. Herein, we disclosed an organocatalytic strategy for highly practical and enantioselective sulfinylation of alcohols and amines through the activation of sulfinates by forming mixed sulfinic anhydrides. Tuning the structure of the reactive species with sterically congested moieties, a simple, naturally occurring quinine catalyst effectively controls the chemo- and enantioselectivity over the nucleophilic S–O and S–N bond constructions, affording a wide range of chiral sulfinyl derivatives with excellent optical purities. Notably, the protocol readily facilitates the coupling with various natural products and commercial drugs that could offer an attractive strategy for the late-stage diversification of important biologically intriguing molecules.