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Updated: Jul 29, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Hydroxyalkylation of conjugated nitroalkenes with activated nonenolizable carbonyl compounds
Indubhusan Deb1, Mamta Dadwal, Shaikh M Mobin
1Department of Chemistry, Indian Institute of Technology, Bombay, Mumbai 400 076, India.
Abstract:
[reaction: see text] The Morita-Baylis-Hillman reaction of a variety of conjugated nitroalkenes with activated nonenolizable carbonyl compounds such as glyoxylate, trifluoropyruvate, pyruvaldehyde, and ninhydrin in the presence of 40-100 mol % of DMAP in acetonitrile or 100 mol % of imidazole in CHCl(3) or THF provided the adducts in decent to good yields. In most cases, the reactions catalyzed by DMAP in acetonitrile were faster and provided the desired MBH adducts in higher yields as compared to the imidazole catalyzed reactions.
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