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

被引：95

作者：

Li, Hui ^{[1
]}

Zhang, Fu-Min ^{[1
]}

Tu, Yong-Qiang ^{[1
]}

Zhang, Qing-Wei ^{[1
]}

Chen, Zhi-Min ^{[1
]}

Chen, Zhi-Hua ^{[1
]}

Li, Jian ^{[1
]}

机构：

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

来源：

CHEMICAL SCIENCE | 2011年 / 2卷 / 09期

关键词：

HIGHLY EFFICIENT SYNTHESIS; RING EXPANSION; ASYMMETRIC BROMOLACTONIZATION; HYDROXY EPOXIDES; BRONSTED ACID; STEREOSELECTIVE CONSTRUCTION; SEMIPINACOL REARRANGEMENT; ALLYLIC ALCOHOLS; BROMINATION; CATALYSIS;

D O I：

10.1039/c1sc00295c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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

引用

页码：1839 / 1841

页数：3

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