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An asymmetric organocatalytic vinylogous Mannich reaction of 3-methyl-5-arylfuran-2(3H)-ones with N-(2-pyridinesulfonyl) imines: enantioselective synthesis of δ-amino γ,γ-disubstituted butenolides.
Organic & Biomolecular Chemistry 2018 March 8
An asymmetric organocatalytic vinylogous Mannich reaction of 3-methyl-5-arylfuran-2(3H)-ones with N-(2-pyridinesulfonyl)imines has been developed with 5 mol% thiourea-tertiary amine as the catalyst. A series of δ-amino γ,γ-disubstituted butenolides bearing adjacent quaternary and tertiary stereocenters are efficiently obtained with satisfactory results (up to 90% yield, 90 : 10 dr, and 95 : 5 er).
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