Copper-Mediated Coupling of 1,1-Dibromo-1-alkenes with Nitrogen Nucleophiles: A General Method for the Synthesis of Ynamides

被引:204
作者
Coste, Alexis [1 ]
Karthikeyan, Ganesan [1 ]
Couty, Francois [1 ]
Evano, Gwilherm [1 ]
机构
[1] Univ Versailles St Quentin Yvelines, Inst Lavoisier Versailles, CNRS, UMR 8180, F-78035 Versailles, France
关键词
copper; cross-coupling; dibromoalkenes; homogeneous catalysis; ynamides; RING-CLOSING METATHESIS; N-FUNCTIONALIZED; 1-ALKYNYLAMIDES; AXIALLY CHIRAL ANILIDES; INTRAMOLECULAR AMIDATION; CATALYZED CYCLIZATION; ALKYNYL BROMIDES; DERIVATIVES; 1,6-DIYNES; CYCLOADDITIONS; CHEMISTRY;
D O I
10.1002/anie.200901099
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Mild reaction conditions are the advantage of the title reaction, which allows straightforward entry to a variety of ynamides starting from readily available 1,1-dibromo-1- alkenes, which act as attractive alkynylating agents (see scheme; EWG=electron-withdrawing group, DMF=N,Ndimethylformamide). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4381 / 4385
页数:5
相关论文
共 75 条
[51]   Total Synthesis of Chaetominine [J].
Toumi, Mathieu ;
Couty, Frangois ;
Marrot, Jerome ;
Evano, Gwilherm .
ORGANIC LETTERS, 2008, 10 (21) :5027-5030
[52]   Eight-step total synthesis of the cyclopeptide alkaloid mucronine E [J].
Toumi, Mathieu ;
Couty, Francois ;
Evano, Gwilherm .
SYNLETT, 2008, (01) :29-32
[53]   Total synthesis of the cyclopeptide alkaloid abyssenine A. Application of inter- and intramolecular copper-mediated coupling reactions in organic synthesis [J].
Toumi, Mathieu ;
Couty, Francois ;
Evano, Gwilherm .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (24) :9003-9009
[54]   Total synthesis of paliurine F [J].
Toumi, Mathieu ;
Couty, Francois ;
Evano, Gwilherm .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (04) :572-575
[55]  
Tracey M.R., 2005, Science of Synthesis, V21, P387
[56]   CHEMICAL AND BIOCHEMICAL-STUDIES OF 2-PROPYNYLPYRROLIDINE DERIVATIVES - RESTRICTED-ROTATION ANALOGS OF N-METHYL-N-(1-METHYL-4-PYRROLIDINO-2-BUTYNYL)ACETAMIDE (BM-5) [J].
TRYBULSKI, EJ ;
KRAMSS, RH ;
MANGANO, RM ;
RUSINKO, A .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (12) :3190-3198
[57]   Ruthenium-catalyzed [2+2] cycloadditions of bicyclic alkenes and ynamides [J].
Villeneuve, K ;
Riddell, N ;
Tam, W .
TETRAHEDRON, 2006, 62 (16) :3823-3836
[58]  
Witulski B, 2000, SYNLETT, P1793
[59]   Stereospecific synthesis of chiral N-(ethynyl)allylglycines and their use in highly stereoselective intramolecular Pauson-Khand reactions [J].
Witulski, B ;
Gossmann, M .
CHEMICAL COMMUNICATIONS, 1999, (18) :1879-1880
[60]   Chemo- and regioselective crossed alkyne cyclotrimerisation of 1,6-diynes with terminal monoalkynes mediated by Grubbs' catalyst or Wilkinson's catalyst [J].
Witulski, B ;
Stengel, T ;
Fernández-Hernández, JM .
CHEMICAL COMMUNICATIONS, 2000, (19) :1965-1966