N-Heterocyclic Carbene-Catalyzed [2+2+2] Annulation of Allenoates with Trifluoromethylketones

被引：37

作者：

Sun Lihui ^{[1
]}

Wang Tong ^{[1
]}

Ye Song ^{[1
]}

机构：

[1] Chinese Acad Sci, Inst Chem, Beijing Natl Lab Mol Sci, CAS Key Lab Mol Recognit & Funct, Beijing 100190, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2012年 / 30卷 / 01期

关键词：

NHC-catalyzed; 2+2+2] annulations; allenoates; trifluoromethylketones; ELECTRON-DEFICIENT OLEFINS; BAYLIS-HILLMAN REACTION; ONE-POT SYNTHESIS; 3+2 CYCLOADDITION; ALLENIC ESTERS; NUCLEOPHILIC CARBENES; PHOSPHINE; ALDEHYDES; IMINES; KETONES;

D O I：

10.1002/cjoc.201100383

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In contrast with the reported phosphine- and DABCO-catalyzed [3+2] and [2+2] annulation of allenoates with trifluoromethylketone, the [2+2+2] annulation of allenoates and two molecules of trifluoromethylketone was found under the condition of N-heterocyclic carbene catalysis.

引用

页码：190 / 194

页数：5

共 78 条

[21] Amine-catalyzed coupling of allenic esters to α,β-unsaturated carbonyls [J].

Evans, CA ;

Miller, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (41) :12394-12395

[22]

Fernández R, 1998, ANGEW CHEM INT EDIT, V37, P3428, DOI 10.1002/(SICI)1521-3773(19981231)37:24<3428::AID-ANIE3428>3.0.CO

[23]

2-P

[24] Umpolung of Michael acceptors catalyzed by N-heterocyclic carbenes [J].

Fischer, C ;

Smith, SW ;

Powell, DA ;

Fu, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (05) :1472-1473

[25] Beyond the Aza-Morita-Baylis-Hillman Reaction: Lewis Base-Catalyzed Reactions of N-Boc-imines with Ethyl 2,3-Butadienoate [J].

Guan, Xiao-Yang ;

Wei, Yin ;

Shi, Min .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (16) :6343-6346

[26] N-heterocyclic carbene catalyzed Aza-Morita-Baylis-Hillman reaction of cyclic enones with N-tosylarylimines [J].

He, Lin ;

Jian, Teng-Yue ;

Ye, Song .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (19) :7466-7468

[27] Phosphine-catalyzed synthesis of highly functionalized coumarins [J].

Henry, Christopher E. ;

Kwon, Ohyun .

ORGANIC LETTERS, 2007, 9 (16) :3069-3072

[28] Enantioselective benzoin condensation catalyzed by bifunctional N-heterocyclic carbenes [J].

Huang XueLiang ;

Ye Song .

CHINESE SCIENCE BULLETIN, 2010, 55 (17) :1753-1757

[29] ANALOGOUS ALPHA,ALPHA'-BIS-CARBENOID TRIPLY BONDED SPECIES - SYNTHESIS OF A STABLE LAMBDA-3-PHOSPHINOCARBENE LAMBDA-5-PHOSPHAACETYLENE [J].

IGAU, A ;

GRUTZMACHER, H ;

BACEIREDO, A ;

BERTRAND, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (19) :6463-6466

[30] Asymmetric Total Synthesis of the Iridoid β-Glucoside (+)-Geniposide via Phosphine Organocatalysis [J].

Jones, Regan A. ;

Krische, Michael J. .

ORGANIC LETTERS, 2009, 11 (08) :1849-1851

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