Intermolecular Asymmetric Reductive Aldol Reaction

T. Shiomi; H. Nishiyama

doi:10.1055/s-2007-968663

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Synfacts 2007(7): 0730-0730
DOI: 10.1055/s-2007-968663

Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions

Intermolecular Asymmetric Reductive Aldol Reaction

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
T. Shiomi, H. Nishiyama*
Nagoya University, Japan

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Publication History

Publication Date:
22 June 2007 (online)

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Significance

This is a valuable report on the reductive aldol reaction of conjugated esters with ketones. Tertiary alcohols are generated in this reaction with up to 98% ee when acetone is used as the ketone. The rhodium (Phebox) complex is the catalyst used to obtain high selectivities. A variety of reductants were screened with MePh₂SiH giving the best results. Various esters can be used and reasonable diastereoselectivities accompany the high ee values when unsymmetrical ketones are used.