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Synfacts 2007(1): 0052-0052  
DOI: 10.1055/s-2006-955726
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Resolution of Ketone Nitroaldol Products

Contributor(s): Mark Lautens, Andrew Martins
S-y. Tosaki, K. Hara, V. Gnanadesikan, H. Morimoto, S. Harada, M. Sugita, N. Yamagiwa, S. Matsunaga*, M. Shibasaki*
The University of Tokyo, Japan
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Publication History

Publication Date:
15 December 2006 (online)

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Significance

Using a mixture of lanthanum-based bimetallic catalysts, a variety of ketone nitro­aldol products underwent a stereoablative resolution to a single enantiomer plus the parent ketone and nitromethane. The yields were generally fair, while enantioselectivities were generally excellent, allowing access to a variety of chiral nitro-containing products. The synthetic utility of the products was demonstrated by the conversion of the nitro group into interesting and/or useful functional groups.