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Synfacts 2010(11): 1276-1276  
DOI: 10.1055/s-0030-1258799
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Reductive Coupling of Alkynes and Imines

Contributor(s): Mark Lautens, Jane Panteleev
C.-Y. Zhou, S.-F. Zhu, L.-X. Wang, Q.-L. Zhou*
State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Tianjin, P. R. of China
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Publication History

Publication Date:
21 October 2010 (online)

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Significance

The authors report an enantioselective reductive coupling of alkynes and imines under nickel catalysis using diethylzinc as a reductant. Recently, Krische reported a similar reduc-tive coupling achieved using rhodium and ­iridium catalysts and hydrogen as reducing agent (J. Am. Chem. Soc. 2005, 127, 11269; J. Am. Chem. Soc. 2007, 129, 12644). This work does present a considerable advance in the use of nickel in this transformation as earlier nickel-catalyzed processes are limited to alkylative coupling and the use of carbonyl electrophiles.

Review: J. Montgomery Angew. Chem. Int. Ed. 2004, 43, 3890-3908.