au2c00186_si_006.cif (736.06 kB)
Cobalt-Catalyzed Cyclization of Unsaturated N‑Acyl Sulfonamides: a Diverted Mukaiyama Hydration Reaction
dataset
posted on 2022-05-06, 16:05 authored by David
M. Fischer, Moritz Balkenhohl, Erick M. CarreiraThe 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.