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Updated: Feb 9, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
An unusual stereoretentive 1,3-quaternary carbon shift resulting in an enantioselective RhII-catalyzed formal
Kevin X Rodriguez1, Tara C Pilato1, Brandon L Ashfeld1
1Department of Chemistry and Biochemistry , University of Notre Dame , Notre Dame , Indiana 46556 , USA .
Abstract:
Enantioselective quaternary carbon construction in the assembly of cyclopentenones employing a RhII-catalyzed, formal [4+1]-cycloaddition is described. A Rh2(S-TCPTTL)4-catalyzed cyclopropanation of a vinyl ketene with a disubstituted diazo compound initiates a stereoretentive, accelerated ring expansion to provide the cycloadduct in good to excellent yields and enantioselectivity.
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