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

作者: Alexis Coste , Ganesan Karthikeyan , François Couty , Gwilherm Evano

DOI: 10.1002/ANIE.200901099

关键词:

摘要: Mild reaction conditions are the advantage of title reaction, which allows straightforward entry to a variety ynamides starting from readily available 1,1-dibromo-1-alkenes, act as attractive alkynylating agents (see scheme; EWG = electron-withdrawing group, DMF N,N-dimethylformamide).

参考文章(69)
Eugene J. Trybulski, Richard H. Kramss, Richard M. Mangano, Andrew Rusinko, Chemical and biochemical studies of 2-propynylpyrrolidine derivatives. Restricted-rotation analogues of N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide (BM-5). Journal of Medicinal Chemistry. ,vol. 33, pp. 3190- 3198 ,(1990) , 10.1021/JM00174A015
Jason A. Mulder, Richard P. Hsung, Michael O. Frederick, Michael R. Tracey, Craig A. Zificsak, The first stereoselective Ficini-Claisen rearrangement using chiral ynamides. Organic Letters. ,vol. 4, pp. 1383- 1386 ,(2002) , 10.1021/OL020037J
Karin Dooleweerdt, Thomas Ruhland, Troels Skrydstrup, Application of ynamides in the synthesis of 2-amidoindoles. Organic Letters. ,vol. 11, pp. 221- 224 ,(2009) , 10.1021/OL802477D
Yu Zhang, Kyle A DeKorver, Andrew G Lohse, Yan-Shi Zhang, Jian Huang, Richard P Hsung, None, Synthesis of Amidines Using N-Allyl Ynamides. A Palladium-Catalyzed Allyl Transfer Through an Ynamido-π-Allyl Complex Organic Letters. ,vol. 11, pp. 899- 902 ,(2009) , 10.1021/OL802844Z
Manuel Lera, Christopher J. Hayes, A new one-Pot synthesis of alkynylphosphonates Organic Letters. ,vol. 2, pp. 3873- 3875 ,(2000) , 10.1021/OL0066173
Sylvain Couty, Christophe Meyer, Janine Cossy, Gold-catalyzed cycloisomerizations of ene-ynamides Tetrahedron. ,vol. 65, pp. 1809- 1832 ,(2009) , 10.1016/J.TET.2008.10.108
Josephine Yuen, Yuan-Qing Fang, Mark Lautens, CuI-Catalyzed Tandem Intramolecular Amidation Using gem-Dibromovinyl Systems Organic Letters. ,vol. 8, pp. 653- 656 ,(2006) , 10.1021/OL052840U
Alexis Coste, Mathieu Toumi, Karen Wright, Vanessa Razafimahaléo, François Couty, Jérome Marrot, Gwilherm Evano, Copper-catalyzed cyclization of iodo-tryptophans: a straightforward synthesis of pyrroloindoles. Organic Letters. ,vol. 10, pp. 3841- 3844 ,(2008) , 10.1021/OL8015513