Cobalt-Catalyzed Cyclization of Unsaturated -Acyl Sulfonamides: a Diverted Mukaiyama Hydration Reaction

Overview

Journal JACS Au

Publisher American Chemical Society

Specialty Chemistry

Date 2022 Jun 1

PMID 35647594

Authors

David M Fischer

Moritz Balkenhohl

Erick M Carreira

Affiliations

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Abstract

The cycloisomerization of β-, γ-, and δ-unsaturated -acyl sulfonamides to -sulfonyl lactams and imidates is reported. This transformation is effected in the presence of a Co(salen) catalyst using -BuOOH or air as the oxidant. The method shows good functional group tolerance (alkyl, aryl, heteroaryl, ether, -Boc) and furnishes an underexplored class of cyclic building blocks. The strong solvent dependence of the transformation is investigated, and the synthetic versatility of the -sulfonyl imidate product class is highlighted.

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