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Issue 9, 2011
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Enantioselective bromination/semipinacol rearrangement for the synthesis of β-bromoketones containing an all-α-carbon quaternary center

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Abstract

A bromination/semipinacol rearrangement reaction catalyzed by cinchona alkaloid derivatives was developed. With 5 mol% (DHQD)2PYDZ, β-bromoketones containing an all-α-carbon quaternary center, which were synthetically useful but challenging to construct, were obtained in up to 97% yield and 93% ee.

Graphical abstract: Enantioselective bromination/semipinacol rearrangement for the synthesis of β-bromoketones containing an all-α-carbon quaternary center

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Publication details

The article was received on 16 May 2011, accepted on 20 Jun 2011 and first published on 07 Jul 2011


Article type: Edge Article
DOI: 10.1039/C1SC00295C
Citation: Chem. Sci., 2011,2, 1839-1841

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    Enantioselective bromination/semipinacol rearrangement for the synthesis of β-bromoketones containing an all-α-carbon quaternary center

    H. Li, F. Zhang, Y. Tu, Q. Zhang, Z. Chen, Z. Chen and J. Li, Chem. Sci., 2011, 2, 1839
    DOI: 10.1039/C1SC00295C

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