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

Mroczynska, Karina; Dobrzanska, Liliana; Rafinski, Zbigniew

Mroczynska, Karina; Dobrzanska, Liliana; Rafinski, Zbigniew.

Afiliación

Mroczynska K; Nicolaus Copernicus University in Torun, Faculty of Chemistry, 7 Gagarin Street, 87-100 Torun, Poland. payudo@chem.umk.pl.
Dobrzanska L; Nicolaus Copernicus University in Torun, Faculty of Chemistry, 7 Gagarin Street, 87-100 Torun, Poland. payudo@chem.umk.pl.
Rafinski Z; Nicolaus Copernicus University in Torun, Faculty of Chemistry, 7 Gagarin Street, 87-100 Torun, Poland. payudo@chem.umk.pl.

Chem Commun (Camb) ; 60(56): 7176-7179, 2024 Jul 09.

Article en En | MEDLINE | ID: mdl-38904356

ABSTRACT

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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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chem Commun (Camb) Asunto de la revista: QUIMICA Año: 2024 Tipo del documento: Article País de afiliación: Polonia Pais de publicación: Reino Unido

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