Palladium-catalyzed stereoselective synthesis of (E)-β,γ-unsaturated amides

被引：12

作者：

Luo, FT ^{[1
]}

Lu, TY

Xue, CH

机构：

[1] Acad Sinica, Inst Chem, Taipei 11529, Taiwan

[2] Natl Chung Cheng Univ, Dept Biochem & Chem, Chiayi 621, Taiwan

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 39期

关键词：

Suzuki coupling reactions; alkenylborane; 2-bromo-N; N-dimethylacetamide;

D O I：

10.1016/j.tetlet.2003.08.011

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile Suzuki type cross-coupling reaction of alkenylborane with 2-bromo-N,N-dimethylacetamide in the presence of a catalytic amount of tricyclohexylphosphine as the ligand has been demonstrated to be a convenient way for the synthesis of (E)-beta,gamma-unsaturated amides. (C) 2003 Elsevier Ltd. All rights reserved.

引用

收藏

页码：7249 / 7251

页数：3

相关论文

共 10 条

[1] ALPHA-DIAZOPHOSPHONIC ACIDS AS POTENTIAL PHOTOAFFINITY-LABELING REAGENTS - SYNTHESIS, STABILITY, AND PHOTOCHEMISTRY [J].

BARTLETT, PA ;

CARRUTHERS, NI ;

WINTER, BM ;

LONG, KP .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (07) :1284-1291

[2] BASE-INDUCED ALPHA-ALKENYLATION OF ETHYL BROMOACETATE, PHENACYL BROMIDE, AND CHLOROACETONITRILE VIA B-TRANS-1-ALKENYL-9-BORABICYCLO[3.3.1]NONANES [J].

BROWN, HC ;

BHAT, NG ;

CAMPBELL, JB .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (17) :3398-3400

[3] CONVERSION OF ALLYLIC ALCOHOLS TO HOMOLOGOUS AMIDES BY N,N-DIMETHYLFORMAMIDE ACETALS [J].

BUCHI, G ;

CUSHMAN, M ;

WUEST, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (17) :5563-5565

[4] (E)-BETA,GAMMA-UNSATURATED AMIDES FROM (E)-9-ALKENYL-9-BORABICYCLO[3.3.1]NONANE AND N,N-DIALKYL(DIMETHYLSULFURANYLIDENE)ACETAMIDE [J].

DENG, MZ ;

LI, NS ;

HUANG, YZ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (01) :65-66

[5] Magnesium methyl carbonate-activated alkylation of methyl ketones with an omega-halo nitrile, esters, and amides [J].

Hand, ES ;

Johnson, SC ;

Baker, DC .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (05) :1348-1355

[6] AZACARBONYLATIONS AND OXACARBONYLATIONS OF ALLYL PHOSPHATES CATALYZED BY RHODIUM CARBONYL CLUSTER - SELECTIVE SYNTHESIS OF BETA,GAMMA-UNSATURATED AMIDES, ESTERS, AND ACIDS [J].

IMADA, Y ;

SHIBATA, O ;

MURAHASHI, SI .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1993, 451 (1-2) :183-194

[7] Palladium-catalyzed cross-coupling reaction of aryldioxaborolane with 2-bromo-N, N-dimethylacetamide [J].

Lu, TY ;

Xue, CH ;

Luo, FT .

TETRAHEDRON LETTERS, 2003, 44 (08) :1587-1590

[8] RUTHENIUM COMPLEX-CATALYZED CARBONYLATION OF ALLYLIC COMPOUNDS [J].

MITSUDO, T ;

SUZUKI, N ;

KONDO, T ;

WATANABE, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (25) :7759-7765

[9] PALLADIUM-CATALYZED CARBONYLATION OF ALLYLAMINES [J].

MURAHASHI, SI ;

IMADA, Y ;

NISHIMURA, K .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (24) :1578-1579

[10] PALLADIUM-CATALYZED CARBONYLATION OF ALLYLAMINES - SYNTHESIS OF BETA,GAMMA-UNSATURATED AMIDES BY ONE-CARBON HOMOLOGATION OF ALLYLAMINES [J].

MURAHASHI, SI ;

IMADA, Y ;

NISHIMURA, K .

TETRAHEDRON, 1994, 50 (02) :453-464