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Synfacts 2011(7): 0742-0742  
DOI: 10.1055/s-0030-1260652
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Lithium Binaphtholate Catalyzed Direct Asymmetric Aldol-Tishchenko Reaction

Contributor(s): Hisashi Yamamoto, Patrick Brady
T. Ichibakase, M. Nakajima*
Kumamoto University, Japan
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Publication History

Publication Date:
17 June 2011 (online)

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Significance

The direct aldol-Tishchenko reaction of ketones with aldehydes catalyzed by a chiral lithium binaphtholate is described. Initially, a mixture of monobenzoyl 1,3-diols is formed. Subsequent hydrolysis generates the 1,3-diols as single diastereomers and in high yield and enantiomeric excess. The catalyst is inexpensive and can be easily prepared.