American Chemical Society
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Cobalt-Catalyzed Cyclization of Unsaturated N‑Acyl Sulfonamides: a Diverted Mukaiyama Hydration Reaction

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posted on 2022-05-06, 16:05 authored by David M. Fischer, Moritz Balkenhohl, Erick M. Carreira
The cycloisomerization of β-, γ-, and δ-unsaturated N-acyl sulfonamides to N-sulfonyl lactams and imidates is reported. This transformation is effected in the presence of a CoIII(salen) catalyst using t-BuOOH or air as the oxidant. The method shows good functional group tolerance (alkyl, aryl, heteroaryl, ether, N-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 N-sulfonyl imidate product class is highlighted.