Enantioselective synthesis of C3-functionalized 2,1-benzothiazine 2,2-dioxides by N-heterocyclic carbene catalysis
Karina Mroczyńska1, Liliana Dobrzańska1, Zbigniew Rafiński1
1Nicolaus Copernicus University in Toruń, Faculty of Chemistry, 7 Gagarin Street, 87-100 Toruń, Poland. payudo@chem.umk.pl.
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.
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