Direct carbocyclization of aldehydes with alkynes: Combining gold catalysis with aminocatalysis

被引：131

作者：

Binder, Jorg T. ^{[1
]}

Crone, Benedikt ^{[1
]}

Haug, Timm T. ^{[1
]}

Menz, Helge ^{[1
]}

Kirsch, Stefan F. ^{[1
]}

机构：

[1] Tech Univ Munich, Dept Chem, D-85747 Garching, Germany

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 05期

关键词：

D O I：

10.1021/ol800092p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A combination of gold(l) complexes and amine bases catalyzes the 5-exo-dig cyclization of formyl alkynes. This direct alpha-functionalization of aldehydes with unactivated alkynes does not involve the use of preformed enol equivalents.

引用

页码：1025 / 1028

页数：4

共 39 条

[1] Sequential amination/annulation/aromatization reaction of carbonyl compounds and propargylamine: A new one-pot approach to functionalized pyridines [J].

Abbiati, G ;

Arcadi, A ;

Bianchi, G ;

Di Giuseppe, S ;

Marinelli, F ;

Rossi, E .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (18) :6959-6966

[2]

Arcadi A, 2001, ADV SYNTH CATAL, V343, P443, DOI 10.1002/1615-4169(200107)343:5<443::AID-ADSC443>3.3.CO

[3]

2-R

[4] Gold- and copper-catalyzed [4+2] benzannulations between enynal or enynone units and 2π-systems [J].

Asao, Naoki .

SYNLETT, 2006, (11) :1645-1656

[5] An efficient and simple aminobenzannulation reaction: Pyrrolidine as a trigger for the synthesis of 1-amino-acridines [J].

Belmont, P ;

Belhadj, T .

ORGANIC LETTERS, 2005, 7 (09) :1793-1795

[6] Synthesis of heterocyclic systems by transition-metal-catalyzed cyclization migration reactions -: A diversity-oriented strategy for the construction of spirocyclic 3(2H)-furanones and 3-pyrrolones [J].

Binder, Jorg T. ;

Crone, Benedikt ;

Kirsch, Stefan F. ;

Liebert, Clemence ;

Menz, Helge .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (10) :1636-1647

[7] Synthesis of highly substituted pyrroles via a multimetal-catalyzed rearrangement-condensation-cyclization Domino approach [J].

Binder, JT ;

Kirsch, SF .

ORGANIC LETTERS, 2006, 8 (10) :2151-2153

[8] MERCURY(II) INDUCED CYCLIZATION OF EPSILON-ACETYLENIC CARBONYL-COMPOUNDS ON SOLID SUPPORTS, WITHOUT SOLVENT [J].

BOAVENTURA, MA ;

DROUIN, J .

SYNTHETIC COMMUNICATIONS, 1987, 17 (08) :975-982

[9] 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

[10] 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

← 1 2 3 4 →