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Synfacts 2007(2): 0188-0188  
DOI: 10.1055/s-2006-958974
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

β-Hydroxyenones via Reductive Aldol Coupling of Divinyl Ketones

Contributor(s): Mark Lautens, Frédéric Ménard
S. B. Han, M. J. Krische*
University of Texas at Austin, USA
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Publication History

Publication Date:
23 January 2007 (online)

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Significance

The process described is of particular interest in that the reaction is chemoselective for the least hindered alkene and the resulting hydroxyenone 3 does not undergo overreduction. Moreover, the diastereoselectivity is generally good to excellent, favoring the syn-aldol adducts 3 and 4. The synthetic use of the method was demonstrated by further transformations of the β-hydroxyenones 3b into polypropionate fragments 5 and 6.