Cooperative Copper(I) and Primary Amine Catalyzed Room-Temperature Carbocyclization of Formyl Alkynes

被引：26

作者：

Montaignac, Benjamin ^{[1
,2
]}

Vitale, Maxime R. ^{[1
,2
]}

Ratovelomanana-Vidal, Virginie ^{[1
,2
]}

Michelet, Veronique ^{[1
,2
]}

机构：

[1] Chimie ParisTech, ENSCP, LCF, UMR 7223, F-75005 Paris, France

[2] CNRS, UMR 7223, F-75005 Paris, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 20-21期

关键词：

Copper; Amines; Organocatalysis; Cyclization; CONIA-ENE REACTION; SILYL ENOL ETHERS; TRANSITION-METAL; ENANTIOSELECTIVE SYNTHESIS; ELECTROPHILIC ACTIVATION; GOLD CATALYSIS; CYCLIZATIONS; CYCLOISOMERIZATION; PLATINUM; EFFICIENT;

D O I：

10.1002/ejoc.201100464

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient Cu-I/amine catalytic system is described for the carbocyclization of alpha-disubstituted formylalkynes at room temperature. Merging aminocatalysis to the copper(I)-catalyzed activation of alkynes led to clean carbocyclization of a wide range of functionalized substrates under mild conditions. This novel cooperative catalytic system allowed the formation of a variety of carbo-and heterocycles, including pyrrolidines, in good to excellent yields. Mechanistic aspects of this process are also discussed.

引用

页码：3723 / 3727

页数：5

共 64 条

[11] Electrophilic activation of alkenes by platinum(II):: So much more than a slow version of palladium(II) [J].

Chianese, Anthony R. ;

Lee, Stephen J. ;

Gagne, Michel R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (22) :4042-4059

[12] Synthetic methods for γ-lactam and pyrrole derivatives exploiting a three-component coupling strategy [J].

Clique, B ;

Anselme, C ;

Otto, D ;

Monteiro, N ;

Balme, G .

TETRAHEDRON LETTERS, 2004, 45 (06) :1195-1197

[13]

Clique B, 2002, EUR J ORG CHEM, V2002, P1493

[14] Efficient, transition metal mediated, sequential, two- and three-component coupling reactions for the synthesis of highly substituted five-membered ring carbocycles [J].

Coia, Nicolas ;

Bouyssi, Didier ;

Balme, Genevieve .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (19) :3158-3165

[15]

CONIA JM, 1975, SYNTHESIS-STUTTGART, P1

[16] Transition-metal-promoted 6-endo-dig cyclization of aromatic enynes:: rapid synthesis of functionalized naphthalenes [J].

Dankwardt, JW .

TETRAHEDRON LETTERS, 2001, 42 (34) :5809-5812

[17] Addition of Metal Enolate Derivatives to Unactivated Carbon-Carbon Multiple Bonds [J].

Denes, Fabrice ;

Perez-Luna, Alejandro ;

Chemla, Fabrice .

CHEMICAL REVIEWS, 2010, 110 (04) :2366-2447

[18] Lewis acid- and organocatalyst-cocatalyzed multicomponent reactions of 2-alkynylbenzaldehydes, amines, and ketones [J].

Ding, Qiuping ;

Wu, Jie .

ORGANIC LETTERS, 2007, 9 (24) :4959-4962

[19] Asymmetric cycloisomerization of 1,6-and 1,7-enynes by transition-metal catalysts [J].

Fairlamb, IJS .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (09) :1048-1052

[20] Copper-catalyzed cycloisomerizations of 5-En-1-yn-3-ols [J].

Fehr, C ;

Farris, I ;

Sommer, H .

ORGANIC LETTERS, 2006, 8 (09) :1839-1841

← 1 2 3 4 5 6 7 →