4.8 Article

Organocatalytic Asymmetric Halogenation/Semipinacol Rearrangement: Highly Efficient Synthesis of Chiral α-Oxa-Quaternary β-Haloketones

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 23, Pages 8818-8821

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja201794v

Keywords

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Funding

  1. NSFC [20921120404, 20732002, 20972059]
  2. 973 program [2010CB833200]
  3. MOE
  4. fundamental research funds for the central universities [lzujbky-2010-k09, lzujbky-2009-76, lzujbky-2009-158]

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A novel asymmetric halogenation/semipinacol rearrangement reaction catalyzed by cinchona alkaloid derivatives was developed. Two types of beta-haloketones (X = Br, Cl) were obtained with up to 95% yield and 99% enantiomeric excess. The desired (+) and (-) enantiomers of the beta-haloketones were readily obtained.

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