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Updated: Jul 20, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Stereoselective synthesis of highly functionalized nitrocyclopropanes via organocatalyic conjugate addition to
Séamus H McCooey1, Thomas McCabe, Stephen J Connon
1Centre for Synthesis and Chemical Biology and School of Chemistry, University of Dublin, Trinity College, Dublin 2, Ireland.
Abstract:
A convenient and novel one-pot organocatalytic methodology for the stereoselective synthesis of highly functionalized nitrocyclopropanes is reported. The addition of dimethyl chloromalonate to a variety of nitroolefins catalyzed by tertiary amines leads to a Michael adduct which cyclizes to form the cyclopropane in the presence of DBU under carefully controlled reaction conditions with outstanding diastereoselectivity.
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