Modular Pyridine Synthesis from Oximes and Enals through Synergistic Copper/Iminium Catalysis

被引：266

作者：

Wei, Ye ^{[1
]}

Yoshikai, Naohiko ^{[1
]}

机构：

[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 10期

基金：

新加坡国家研究基金会;

关键词：

ONE-POT SYNTHESIS; TRANSITION-METAL; ALPHA; BETA-UNSATURATED KETOXIMES; ALDEHYDES; ALKYNES; COMBINATION; ALKYLATION; SALTS; 2,4,6-TRIARYLPYRIDINES; CYCLOADDITION;

D O I：

10.1021/ja312346s

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We describe here a [3+3]-type condensation reaction of O-acetyl ketoximes and alpha,beta-unsaturated aldehydes that is synergistically catalyzed by a copper(I) salt and a secondary ammonium salt (or amine). This redox-neutral reaction allows modular synthesis of a variety of substituted pyridines under mild conditions with tolerance of a broad range of functional groups. The reaction is driven by a merger of iminium catalysis and redox activity of the copper catalyst, which would initially reduce the oxime N-O bond to generate a nucleophilic copper(II) enamide and later oxidize a dihydropyridine intermediate to the pyridine product.

引用

页码：3756 / 3759

页数：4

共 54 条

[1] Catalytic Enantioselective β-Alkylation of α,β-Unsaturated Aldehydes by Combination of Transition-Metal- and Aminocatalysis: Total Synthesis of Bisabolane Sesquiterpenes [J].

Afewerki, Samson ;

Breistein, Palle ;

Pirttila, Kristian ;

Deiana, Luca ;

Dziedzic, Pawel ;

Ibrahem, Ismail ;

Cordova, Armando .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (32) :8784-8788

[2] Use of β,γ-Unsaturated α-Ketocarbonyls for a Totally Regioselective Oxidative Multicomponent Synthesis of Polyfunctionalized Pyridines [J].

Allais, Christophe ;

Constantieux, Thierry ;

Rodriguez, Jean .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (47) :12945-12948

[3] Synergistic catalysis: A powerful synthetic strategy for new reaction development [J].

Allen, Anna E. ;

MacMillan, David W. C. .

CHEMICAL SCIENCE, 2012, 3 (03) :633-658

[4] Enantioselective α-Arylation of Aldehydes via the Productive Merger of lodonium Salts and Organocatalysis [J].

Allen, Anna E. ;

MacMillan, David W. C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (12) :4260-4263

[5] The Productive Merger of Iodonium Salts and Organocatalysis: A Non-photolytic Approach to the Enantioselective α-Trifluoromethylation of Aldehydes [J].

Allen, Anna E. ;

MacMillan, David W. C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (14) :4986-+

[6] The bohimann-rahtz pyridine synthesis: From discovery to applications [J].

Bagley, Mark C. ;

Glover, Christian ;

Merritt, Eleanor A. .

SYNLETT, 2007, (16) :2459-2482

[7] Gold-catalyzed intermolecular Hetero-Dehydro-Diels-Alder cycloaddition of captodative dienynes with nitriles:: A new reaction and regioselective direct access to pyridines [J].

Barluenga, Jose ;

Fernandez-Rodriguez, Manuel Angel ;

Garcia-Garcia, Patricia ;

Aguilar, Enrique .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (09) :2764-+

[8] Microwave-Promoted and Lewis Acid Catalysed Synthesis of 2,4,6-Triarylpyridines Using Urea as Benign Source of Ammonia [J].

Borthakur, Moytirima ;

Dutta, Mandakini ;

Gogoi, Shyamalee ;

Boruah, Romesh C. .

SYNLETT, 2008, (20) :3125-3128

[9] Synthesis of Pyridine and Dihydropyridine Derivatives by Regio- and Stereoselective Addition to N-Activated Pyridines [J].

Bull, James A. ;

Mousseau, James J. ;

Pelletier, Guillaume ;

Charette, Andre B. .

CHEMICAL REVIEWS, 2012, 112 (05) :2642-2713

[10] Three-Component Coupling Sequence for the Regiospecific Synthesis of Substituted Pyridines [J].

Chen, Ming Z. ;

Micalizio, Glenn C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (02) :1352-1356

← 1 2 3 4 5 6 →