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有机催化不对称卤化/半频哪醇重排:手性α-氧代季碳β-卤代酮的高效合成。

Organocatalytic asymmetric halogenation/semipinacol rearrangement: highly efficient synthesis of chiral α-oxa-quaternary β-haloketones.

机构信息

State Key Laboratory of Applied Organic Chemistry & Department of Chemistry, Lanzhou University, Lanzhou 730000, PR China.

出版信息

J Am Chem Soc. 2011 Jun 15;133(23):8818-21. doi: 10.1021/ja201794v. Epub 2011 May 11.

Abstract

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

摘要

发展了一种由金鸡纳生物碱衍生物催化的新型不对称卤化/半频哪醇重排反应。两种类型的β-卤代酮(X = Br,Cl)以高达 95%的产率和 99%的对映体过量得到。易于获得所需的(+)和(-)对映体的β-卤代酮。

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