Stereoselective construction of all-carbon quaternary center by means of chiral phosphoric acid: highly enantioselective Friedel-Crafts reaction of indoles with β,β-disubstituted nitroalkenes

被引：76

作者：

Mori, Keiji ^{[1
]}

Wakazawa, Manari ^{[1
]}

Akiyama, Takahiko ^{[1
]}

机构：

[1] Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan

来源：

CHEMICAL SCIENCE | 2014年 / 5卷 / 05期

关键词：

ORGANOCATALYTIC MICHAEL ADDITION; BOND-FORMING REACTIONS; MANNICH-TYPE REACTION; BRONSTED ACID; CONJUGATE ADDITION; STEREOGENIC CENTERS; ISATYLIDENE-3-ACETALDEHYDES APPLICATION; 1,3-DIPOLAR CYCLOADDITION; EFFICIENT ORGANOCATALYSTS; 1,4-ADDITION REACTIONS;

D O I：

10.1039/c3sc53542h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We describe herein a chiral phosphoric acid catalyzed Friedel-Crafts reaction of indoles with beta-alkoxycarbonyl-beta-disubstituted nitroalkenes. A wide variety of substrates participated in this reaction to afford indoles having all-carbon quaternary centers with excellent selectivities ( up to 97% ee). Further investigation suggested that the olefin geometry and the employment of NH-indole derivatives are responsible for both reactivity and selectivity.

引用

页码：1799 / 1803

页数：5

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