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Issue 8, 2019
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Kinetic resolution of β-ketoesters with quaternary stereocenters via a carbene-catalyzed benzoin reaction

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Abstract

Chiral β-ketoesters bearing fully substituted carbon centers are important building blocks in organic synthesis. Mono-substituted ketoesters have been widely used to synthesize the above compounds through asymmetric additions or substitutions. The limitations of these protocols mainly exist in the substrate scopes, and α-methyl or α-fluoro-substituted β-ketoesters or acetyl acetates are frequently used owing to their relatively higher reactivity. To break through this limitation, we employed N-heterocyclic carbene-catalyzed kinetic resolution to achieve the access to enantioenriched β-ketoesters with quaternary stereocenters. Sterically more bulky groups such as benzyl, allyl, phenyl and cyclopropyl groups are all tolerated using this method.

Graphical abstract: Kinetic resolution of β-ketoesters with quaternary stereocenters via a carbene-catalyzed benzoin reaction

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Publication details

The article was received on 04 Oct 2018, accepted on 28 Jan 2019 and first published on 28 Jan 2019


Article type: Paper
DOI: 10.1039/C8OB02468E
Citation: Org. Biomol. Chem., 2019,17, 2169-2173

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    Kinetic resolution of β-ketoesters with quaternary stereocenters via a carbene-catalyzed benzoin reaction

    S. T. Zehra, G. Zhang, S. Yang and X. Fang, Org. Biomol. Chem., 2019, 17, 2169
    DOI: 10.1039/C8OB02468E

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