Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation of β-ketoesters: An Unusual Counterion Effect

被引：65

作者：

Trost, Barry M. ^{[1
]}

Schaeffner, Benjamin ^{[1
]}

Osipov, Maksim ^{[1
]}

Wilton, Donna A. A. ^{[1
]}

机构：

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 15期

关键词：

allylic compounds; asymmetric catalysis; palladium; beta-ketoesters; ENANTIOSELECTIVE SYNTHESIS; PROCHIRAL NUCLEOPHILES; ALLYLATION; CONSTRUCTION; CREATION; LITHIUM; ESTERS;

D O I：

10.1002/anie.201007803

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Buy one, get one free: Both enantiomers of tetralone and indanone derivatives are available in a one-pot procedure from allyl chloroformate and their β-ketoesters by using the same catalyst system (see scheme; dba=dibenzylideneacetone, 1,2-DCE=1,2-dichloroethane, THF=tetrahydrofuran). The details of this remarkable effect were investigated by performing scavenging experiments and a variety of substrates were successfully used in the procedure. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：3548 / 3551

页数：4

共 49 条

[1] EFFECT OF LITHIUM COMPLEXATION BY 12-CROWN-4 ON THE REGIOSELECTIVITY OF THE ATTACK OF GEM-DICHLOROALLYL-LITHIUM ON SOME CARBONYL-COMPOUNDS [J].