An Olefination via Ruthenium-Catalyzed Decarbonylative Addition of Aldehydes to Terminal Alkynes

被引：128

作者：

Guo, Xiangyu ^{[1
]}

Wang, Jun ^{[1
]}

Li, Chao-Jun ^{[1
]}

机构：

[1] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 42期

基金：

加拿大自然科学与工程研究理事会;

关键词：

WADSWORTH-EMMONS OLEFINATION; ATOM ECONOMY;

D O I：

10.1021/ja906265a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A ruthenium-catatyzed olefination via decarbonylative addition of aldehydes; and alkynes has been developed. A strong electronic effect and high chemoselectivity between aromatic and aliphatic aldehydes were observed in this reaction.

引用

页码：15092 / +

页数：4

共 31 条

[1] Mechanistic Manifold and New Developments of the Julia-Kocienski Reaction [J].

Aissa, Christophe .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (12) :1831-1844

[2] Grubbs' Ruthenium-Carbenes Beyond the Metathesis Reaction: Less Conventional Non-Metathetic Utility [J].

Alcaide, Benito ;

Almendros, Pedro ;

Luna, Amparo .

CHEMICAL REVIEWS, 2009, 109 (08) :3817-3858

[3] On the use of the modified Julia olefination for bryostatin synthesis [J].

Allen, Joanne V. ;

Green, Anthony P. ;

Hardy, Simon ;

Heron, Nicola M. ;

Lee, Alan T. L. ;

Thomas, Eric J. .

TETRAHEDRON LETTERS, 2008, 49 (44) :6352-6355

[4] Total synthesis of (+)-dactylolide through an efficient sequential peterson olefination and prins cyclization reaction [J].

Aubele, DL ;

Wan, SY ;

Floreancig, PE .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (22) :3485-3488

[5] Use of lithium hexafluoroisopropoxide as a mild base for Horner-Wadsworth-Emmons olefination of epimerizable aldehydes [J].

Blasdel, LK ;

Myers, AG .

ORGANIC LETTERS, 2005, 7 (19) :4281-4283

[6] Scope and limitations of the Julia-Kocienski reaction with fluorinated sulfonylesters [J].

Calata, Charlene ;

Catel, Jean-Marie ;

Pfund, Emmanuel ;

Lequeux, Thierry .

TETRAHEDRON, 2009, 65 (20) :3967-3973

[7] CATALYTIC DIMERIZATION OF ALKENES BY NICKEL-COMPLEXES IN ORGANOCHLOROALUMINATE MOLTEN-SALTS [J].

CHAUVIN, Y ;

GILBERT, B ;

GUIBARD, I .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (23) :1715-1716

[8] Alkenol-alkyne cross metathesis [J].

Clark, Daniel A. ;

Clark, Joseph R. ;

Diver, Steven T. .

ORGANIC LETTERS, 2008, 10 (10) :2055-2058

[9] Inter- and intramolecular Horner-Wadsworth-Emmons reactions of 5-(diethoxyphosphoryl)-1-acyl-2-alkyl(aryl)-2,3-dihydro-4-pyridones [J].

Comins, DL ;

Ollinger, CG .

TETRAHEDRON LETTERS, 2001, 42 (25) :4115-4118

[10]

Dumeunier R., 2004, Modern Carbonyl Olefination

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