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

被引：143

作者：

Chen, Zhi-Min

Zhang, Qing-Wei

Chen, Zhi-Hua

Li, Hui

Tu, Yong-Qiang ^{[1
]}

Zhang, Fu-Min

Tian, Jin-Miao

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 23期

关键词：

ENANTIOSELECTIVE HALOCYCLIZATION; SEMIPINACOL REARRANGEMENT; HYDROXY EPOXIDES; ALLYLIC ALCOHOLS; BRONSTED ACID; BROMOLACTONIZATION; FLUORINATION; ENONES; TRIFLUOROMETHYLATION; COMPLEXES;

D O I：

10.1021/ja201794v

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：8818 / 8821

页数：4

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