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Issue 5, 2014
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Enantioenriched β-lactone and aldol-type products from regiodivergent carbonylation of racemic cis-epoxides

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Abstract

A new carbonylation catalyst is reported that provides enantioenriched β-lactones and aldol-type products from the carbonylative ring-expansion of racemic cis-epoxides. Detailed analysis of the reaction demonstrates that the epoxide substrates undergo regiodivergent carbonylation reactions instead of traditional kinetic resolutions. This new catalytic system was applied to the synthesis of a key fragment of the antibiotic Globomycin.

Graphical abstract: Enantioenriched β-lactone and aldol-type products from regiodivergent carbonylation of racemic cis-epoxides

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Publication details

The article was received on 08 Jan 2014, accepted on 19 Feb 2014 and first published on 28 Feb 2014


Article type: Edge Article
DOI: 10.1039/C4SC00075G
Citation: Chem. Sci., 2014,5, 1928-1933
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    Enantioenriched β-lactone and aldol-type products from regiodivergent carbonylation of racemic cis-epoxides

    M. Mulzer, W. C. Ellis, E. B. Lobkovsky and G. W. Coates, Chem. Sci., 2014, 5, 1928
    DOI: 10.1039/C4SC00075G

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