Direct Asymmetric α-Allylation of Aldehydes with Simple Allylic Alcohols Enabled by the Concerted Action of Three Different Catalysts

被引：268

作者：

Jiang, Gaoxi ^{[1
]}

List, Benjamin ^{[1
]}

机构：

[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 40期

关键词：

allylation; allylic alcohol; chiral counteranions; palladium; phosphates; TRANSITION-METAL CATALYSIS; DEHYDRATIVE ALLYLATION; PALLADIUM; ALKYLATION; ACID; SUBSTITUTION; EPOXIDATION; CONVERSION; LIGANDS; REGIO;

D O I：

10.1002/anie.201103263

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Triple catalysis: The title reaction between α-branched aldehydes and allylic alcohols, which generates all-carbon quaternary stereogenic centers, constitutes the first asymmetric Tsuji-Trost-type α-allylation of carbonyl compounds with allylic alcohol (see scheme). This reaction is catalyzed by three different species, [Pd(PPh3)4], the chiral Brønsted acid TRIP, and benzhydryl amine. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：9471 / 9474

页数：4

共 67 条

[61] Asymmetric counteranion-directed catalysis for the epoxidation of enals [J].

Wang, Xingwang ;

List, Benjamin .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (06) :1119-1122

[62] Transition Metal-Catalyzed Decarboxylative Allylation and Benzylation Reactions [J].

Weaver, Jimmie D. ;

Recio, Antonio, III ;

Grenning, Alexander J. ;

Tunge, Jon A. .

CHEMICAL REVIEWS, 2011, 111 (03) :1846-1913

[63] Regioselective and enantioselective iridium-catalyzed allylation of enamines [J].

Weix, Daniel J. ;

Hartwig, John F. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (25) :7720-+

[64] Dual Amine- and Bronsted Acid-Catalyzed α-Allylic Alkylation of Aldehydes [J].

Xu, Li-Wen ;

Gao, Guang ;

Gu, Feng-Lei ;

Sheng, Hao ;

Li, Li ;

Lai, Guo-Qiao ;

Jiang, Jian-Xiong .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (09) :1441-1445

[65] Iridium-catalyzed, asymmetric amination of allylic alcohols activated by Lewis acids [J].

Yamashita, Yasuhiro ;

Gopalarathnam, Apsara ;

Hartwig, John F. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (24) :7508-+

[66] Regio- and stereoselectivity in palladium(0)-catalyzed allylation of anilines using allylic alcohols directly [J].

Yang, SC ;

Tsai, YC .

ORGANOMETALLICS, 2001, 20 (04) :763-770

[67] When Organocatalysis Meets Transition-Metal Catalysis [J].

Zhong, Cheng ;

Shi, Xiaodong .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (16) :2999-3025

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