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Issue 12, 2018
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An unusual stereoretentive 1,3-quaternary carbon shift resulting in an enantioselective RhII-catalyzed formal [4+1]-cycloaddition between diazo compounds and vinyl ketenes

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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.

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

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Publication details

The article was received on 03 Jan 2018, accepted on 17 Feb 2018 and first published on 19 Feb 2018


Article type: Edge Article
DOI: 10.1039/C8SC00020D
Citation: Chem. Sci., 2018,9, 3221-3226
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    An unusual stereoretentive 1,3-quaternary carbon shift resulting in an enantioselective RhII-catalyzed formal [4+1]-cycloaddition between diazo compounds and vinyl ketenes

    K. X. Rodriguez, T. C. Pilato and B. L. Ashfeld, Chem. Sci., 2018, 9, 3221
    DOI: 10.1039/C8SC00020D

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