Palladium-catalyzed enantioselective C-3 allylation of 3-substituted-1H-indoles using trialkylboranes

被引：452

作者：

Trost, Barry M. ^{[1
]}

Quancard, Jean ^{[1
]}

机构：

[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 19期

关键词：

D O I：

10.1021/ja0608139

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We have developed a new enantioselective C-3 allylation of 3-substituted indoles using allyl alcohol and trialkylboranes. Asymmetric syntheses of 3,3-disubstituted indolines and indolenines in enantiomeric excesses up to 90% have been achieved using the bulky borane 9-BBN-C6H13 as the promoter of the reaction. The dependence of the selectivity on the nature of the borane suggests that the boron reagent has a role beyond promoting ionization of the allyl alcohol. A protocol for oxidation of indolenines to oxindoles has also been developed and led to a formal synthesis of (-)-phenserine. Copyright © 2006 American Chemical Society.

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页码：6314 / 6315

页数：2

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