Formal Intermolecular [2+2] Cycloaddition Reaction of Alleneamides with Alkenes via Gold Catalysis

被引：104

作者：

Li, Xiao-Xiao ^{[1
]}

Zhu, Li-Li ^{[1
]}

Zhou, Wen ^{[1
]}

Chen, Zili ^{[1
,2
]}

机构：

[1] Renmin Univ China, Dept Chem, Beijing 100872, Peoples R China

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

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 02期

关键词：

INTRAMOLECULAR HYDROAMINATION; ORGANIC-SYNTHESIS; ALLENES; PLATINUM; DERIVATIVES; ACCESS; 4C+3C; CYCLOISOMERIZATION; HYDROALKOXYLATION; ALLENEDIENES;

D O I：

10.1021/ol202703a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method was developed to construct the densely functionalized cyclobuane adducts through formal intermolecular cycloaddition of alleneamides with electron-rich olefins via gold catalysis, in which vinyl ethers/amides and electron-rich styrenes worked very well. In addition, a series of alleneamide dimerization products were prepared from the same alleneamide substrates.

引用

页码：436 / 439

页数：4

共 63 条

[1] Exploiting [2+2] cycloaddition chemistry: achievements with allenes [J].

Alcaide, Benito ;

Almendros, Pedro ;

Aragoncillo, Cristina .

CHEMICAL SOCIETY REVIEWS, 2010, 39 (02) :783-816

[2] Gold-Catalyzed [4C+2C] Cycloadditions of Allenedienes, including an Enantioselective Version with New Phosphoramidite-Based Catalysts: Mechanistic Aspects of the Divergence between [4C+3C] and [4C+2C] Pathways [J].

Alonso, Isaac ;

Trillo, Beatriz ;

Lopez, Fernando ;

Montserrat, Sergi ;

Ujaque, Gregori ;

Castedo, Luis ;

Lledos, Agusti ;

Mascarenas, Jose L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (36) :13020-13030

[3] Alternative synthetic methods through new developments in catalysis by gold [J].

Arcadi, Antonio .

CHEMICAL REVIEWS, 2008, 108 (08) :3266-3325

[4]

Bach T, 1998, SYNTHESIS-STUTTGART, P683

[5]

Bauslaugh P.G., 1970, SYNTHESIS, P287

[6] Electrophilic activation and cycloisomerization of enynes: A new route to functional cyclopropanes [J].

Bruneau, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (16) :2328-2334

[7] An opened route to 1,3-dimethylenecyclobutanes via sequential ruthenium-catalyzed [2+2] cycloaddition of allenyl boronate and palladium Suzuki coupling [J].

Bustelo, E ;

Guérot, C ;

Hercouet, A ;

Carboni, B ;

Toupet, L ;

Dixneuf, PH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (33) :11582-11583

[8] Highly enantioselective [2+2]-cycloaddition reactions catalyzed by a chiral aluminum bromide complex [J].

Canales, Eda ;

Corey, E. J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (42) :12686-+

[9] Synthesis of dicyclopenta[a,e]pentalenes via a molybdenum carbonyl mediated tandem allenic Pauson-Khand reaction and the X-ray crystal structure of a planar dicyclopenta[a,e]pentalene [J].

Cao, H ;

Van Ornum, SG ;

Deschamps, J ;

Flippen-Anderson, J ;

Laib, F ;

Cook, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (03) :933-943

[10] Hydrogen-bond basicity of the sulfonyl group. The case of strongly basic sulfonamidates RSO(2)N(-)N(+)Me(3) [J].

Chardin, A ;

Laurence, C ;

Berthelot, M ;

Morris, DG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1996, (06) :1047-1051

← 1 2 3 4 5 6 7 →