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Synfacts 2007(4): 0400-0400  
DOI: 10.1055/s-2007-968358
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Preparation of Chiral 1,3-anti-Diols through Catalytic Hydrogenation

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
O. Labeeuw, C. Roche, P. Phansavath*, J.-P. Genêt*
ENSCP, Paris, France
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Publication History

Publication Date:
23 March 2007 (online)

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Significance

A very efficient procedure for the hydrogenation of β-hydroxy ketones to anti-1,3-diols is reported. The use of only 2 mol% RuCl3 is required and the economical use of H2 at 10 bar provides the diols with >90% de. A brief screen of phosphine ligands showed PPh3 to give optimal results, while PCy3 gave syn selectivity! A variety of ketones were successful for this reaction including benzyl-protected alcohols, which were untouched under the conditions. This is a nice fundamental synthesis of 1,3-diols.