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Synfacts 2008(8): 0853-0853  
DOI: 10.1055/s-2008-1077917
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Pd-Catalyzed Aldol Reaction for Formation of Chiral Quaternary Centers

Contributor(s): Mark Lautens, Frédéric Ménard
N. Umebayashi, Y. Hamashima, D. Hashizume, M. Sodeoka*
RIKEN, Wako and Saitama University, Japan
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Publication History

Publication Date:
23 July 2008 (online)

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Significance

The low nucleophilicity of 1,3-di­carbonyl metal enolates and the ready retro-aldol reaction have stalled the development of metal catalysts for asymmetric aldol reactions. The protocol uses overall neutral conditions where only the metal center acts as Lewis acid. Using BINAP as the chiral ligand, the reaction yields protected alcohols directly with excellent enantioselectivity.