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Updated: Mar 14, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Stereoselective Multicomponent Reactions Using Zincate Nucleophiles: β-Dicarbonyl Synthesis and Functionalization
Stephen K Murphy1, Mingshuo Zeng1, Seth B Herzon1,2
1Department of Chemistry, Yale University , New Haven, Connecticut 06520, United States.
Abstract:
A general strategy for conjugate addition-C-acylation that enables the synthesis of enantioenriched β-dicarbonyl compounds is described. A novel method for derivatizing these adducts by stereo- and site-selective zinc-catalyzed addition of alkyllithium reagents is also reported. These reactions can be performed in tandem to achieve an enantio- and diastereoselective four-component coupling. The in situ generation of weakly basic lithium zincate species is central to the success of all three transformations.
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