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Synfacts 2009(6): 0640-0640  
DOI: 10.1055/s-0029-1216782
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

New Ligands for Copper-Catalyzed 1,4-Conjugate Addition Reactions

Contributor(s): Mark Lautens, Jacki Kitching
D.-Y. Zou, Z.-C. Duan, X.-P. Hu*, Z. Zheng*
China Agricultural University, Beijing and Dalian Institute of Chemical Physics, P. R. of China
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Publication History

Publication Date:
25 May 2009 (online)

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Significance

Research involving the 1,4-addition of organometallic reagents to α,β-unsaturated compounds has received considerable attention. In the present paper, the authors describe the synthesis and application of new bis(1-ferrocenylethyl)amine-derived monodentate phosphor­amidite ligands in copper-catalyzed 1,4-conjugate additions. For reactions involving addition to nitro­alkenes, the central chirality in the ligands was found to determine the absolute configuration of the products, while in the addition to cyclo­alkenones the axial chirality in the ligands determined the absolute configuration of the products.

Reviews: A. Alexakis, J. E. Bäckvall, N. Krause, O. Pàmies, M. Diéguez Chem. Rev. 2008, 108, 2796-2823; S. R. Harutyunyan, T. den Hartog, K. Geurts, A. J. Minaard, B. L. Feringa Chem. Rev. 2008, 108, 2824-2852.