Rhodium(II)-Catalyzed Enantioselective C-H Functionalization of Indoles

被引：157

作者：

DeAngelis, Andrew ^{[1
]}

Shurtleff, Valerie W. ^{[1
]}

Dmitrenko, Olga ^{[1
]}

Fox, Joseph M. ^{[1
]}

机构：

[1] Univ Delaware, Dept Chem & Biochem, Brown Labs, Newark, DE 19716 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 06期

关键词：

INTERMOLECULAR REACTIONS; INSERTION REACTIONS; RHODIUM CARBENOIDS; ALPHA-DIAZOESTERS; CARBONYL YLIDES; CYCLOPROPANATION; SELECTIVITY; PROTONATION; PYRROLES; COPPER;

D O I：

10.1021/ja1093309

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A catalytic, enantioselective method for the C-H functionalization of indoles by diazo compounds has been achieved. With catalytic amounts of Rh-2(S-NTTL)(4), the putative Rh-carbene intermediates from alpha-alkyl-alpha-diazoesters react with indoles at C(3) to provide alpha-alkyl-alpha-indolylacetates in high yield and enantioselectivity. From DFT calculations, a mechanism is proposed that involves a Rh-ylide intermediate with oxocarbenium character.

引用

页码：1650 / 1653

页数：4

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