Enantioselective Allylation, Crotylation, and Reverse Prenylation of Substituted Isatins: Iridium-Catalyzed C-C Bond-Forming Transfer Hydrogenation

被引：146

作者：

Itoh, Junji ^{[1
]}

Han, Soo Bong ^{[1
]}

Krische, Michael J. ^{[1
]}

机构：

[1] Univ Texas Austin, Dept Chem & Biochem, Austin, TX 78712 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 34期

关键词：

allylation; crotylation; enantioselectivity; iridium; transfer hydrogenation; ALDEHYDE OXIDATION LEVEL; ASYMMETRIC ALDOL CONDENSATION; BRYOZOAN AMATHIA-CONVOLUTA; ALPHA-HYDROXY ESTERS; CARBONYL ALLYLATION; TERTIARY ALCOHOLS; ALLYLIC AMINES; ORGANOMETALLIC REAGENTS; IMINE VINYLATION; METAL REAGENTS;

D O I：

10.1002/anie.200902328

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Oxindoles with a twist: Transfer hydrogenation of substituted isatins in the presence of allyl acetate, α- methyl allyl acetate, or 1,1,-dimethylallene using an cyclometalated iridium catalyst, provides products of carbonyl allylation, crotylation, and reverse prenylation, respectively, in highly enantiomerically enriched form. These studies represent the first use of activated ketones as electrophilic partners in asymmetric C-C bondforming transfer hydrogenation. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：6313 / 6316

页数：4

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