Palladium-Catalyzed Double Carbopalladation/syn-Insertion Cascade toward a Pragmatic Synthesis of Aminated Polyheterocyclic 1,2-Benzothiazepine 1-Oxides

Abstract

A palladium-catalyzed tandem cyclization reaction was developed, which offers a pragmatic synthesis of aminated tetracyclic 1,2-benzothiazepine 1-oxides bearing a highly fused medium-sized cyclic unit. An acetyl (Ac) group was found to be the optimal protecting group for sulfoximines to reduce the nucleophilic ability of the N atom, thus efficiently suppressing the formation of intramolecular 5-exo-dig cyclization side products. The transformation proceeds through a double syn-carbopalladation/annulation sequence to construct the rigid tetracyclic carbo-heterocyclic framework with excellent chemoselectivity and regioselectivity.

Key words

palladium catalysis - carbopalladation - cascade reaction - polyheterocycles - 1,2-benzothiazepine 1-oxides - sulfoximines

Publication History

Received: 21 August 2022

Accepted after revision: 09 November 2022

Accepted Manuscript online:
09 November 2022

Article published online:
29 November 2022

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