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Synfacts 2010(9): 1040-1040  
DOI: 10.1055/s-0030-1257957
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Dinuclear Nickel Catalyst in 1,4-Addition of α-Ketoanilides to Nitroalkenes

Contributor(s): Mark Lautens, Jane Panteleev
Y. Xu, S. Matsunaga*, M. Shibasaki*
The University of Tokyo and Institute of Microbial Chemistry, Tokyo, Japan
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Publication History

Publication Date:
23 August 2010 (online)

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Significance

The use of α-keto esters as nucleophiles in conjugate addition is uncommon because of their high electrophilicity and thus pre­disposition to self-condensation. This work describes an application of a dinuclear nickel catalyst to address this problem, yielding syn products in moderate to good yields and enantioselectivities. This work is preceded by a report from the Sodeoka group (J. Am. Chem. Soc, 2010, 132, 4036), where similar products are obtained in high anti selectivity.