Synlett 2003(15): 2425-2427  
DOI: 10.1055/s-2003-42125
LETTER
© Georg Thieme Verlag Stuttgart · New York

Efficient Copper-Catalyzed Chemo Selective Conjugate Addition of Aliphatic Amines to α,β-Unsaturated Compounds in Water

Li-Wen Xu, Jing-Wei Li, Chun-Gu Xia*, Shao-Lin Zhou, Xiao-Xue Hu
State key laboratory of Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, 730000, P. R. China
Fax: +86(931)8277088; e-Mail: cgxia@ns.lzb.ac.cn;
Further Information

Publication History

Received 19 September 2003
Publication Date:
21 November 2003 (online)

Abstract

The first environmentally benign, highly efficient, conjugate addition of aliphatic amines to α,β-unsaturated compounds catalyzed by simple copper salts in the green solvent, water is described.

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General Procedure for the aza-Michael Addition Reactions. A mixture of amine (1.2 mmol), α,β-unsaturated compound (1 mmol) and copper salts (5 mol%) in acetonitrile/H2O (1/1) or H2O was kept at r.t. under vigorous stirring for 12 h. After completion of the reaction, the reaction mixture was extracted with EtOAc and purified by using column chromatography on silical gel to obtain pure product. All the known compounds were fully characterized by GC-MS (Agilent 6890N GC/5973N MS, HP-5MS) and usual spectral methods.