An unusual stereoretentive 1,3-quaternary carbon shift resulting in an enantioselective RhII -catalyzed formal [4+1]-cycloaddition between diazo compounds and vinyl ketenes

Chemical Science
Kevin X RodriguezBrandon L Ashfeld

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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Citations

Nov 17, 2020·Frontiers in Chemistry·Mikk Kaasik, Tõnis Kanger

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Methods Mentioned

BETA
X-ray

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