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Synfacts 2006(9): 0922-0922  
DOI: 10.1055/s-2006-949235
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric α-Alkylative Reduction of Ketones with Alcohols

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
G. Onodera, Y. Nishibayashi*, S. Uemura
The University of Tokyo and Kyoto University, Japan
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Publication History

Publication Date:
23 August 2006 (online)

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Significance

A nice sequential reaction was developed in which the first step is the iridium-catalyzed α-alkylation of a ketone followed by a ruthenium-catalyzed hydrogenation of the ketone to an alcohol. The reaction shows good reactivity and the compatibility of having two metal catalysts present in the reaction medium without serious complication. Very high ee values were obtained with decent yields. Various primary alcohols are suitable in this reaction and the authors used a variety of methyl-aryl ketones.