Enantioselective synthesis of C3-functionalized 2,1-benzothiazine 2,2-dioxides by N-heterocyclic carbene catalysis

Abstract

We present herein an approach for the enantioselective C3-functionalization of 2,1-benzothiazine 2,2-dioxides using N-heterocyclic carbene (NHC) catalysis. Our method involves a sequence of [3+3] cycloaddition and ring-opening reactions with different N- and O-nucleophiles, followed by silylation. Overcoming the challenge of selectivity targeting the C3 position, this protocol demonstrates a broad substrate scope and high enantioselectivity. This marks a significant advancement in the field of NHC-catalyzed transformations.