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Synfacts 2006(9): 0918-0918  
DOI: 10.1055/s-2006-949265
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Pd(II)/Sparteine-Catalyzed Mukaiyama Aldol Reaction

Contributor(s): Mark Lautens, Andrew Martins
S-i. Kiyooka*, Y. Takeshita, Y. Tanaka, T. Higaki, Y. Wada
Kochi University, Japan
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Publication History

Publication Date:
23 August 2006 (online)

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Significance

A variety of aldehydes were converted enantioselectively into aldol products upon reaction with a silyl enol ether using a ‘naked’ [(-)-sparteine]Pd(II) catalyst formed in situ. Yields were generally good, with enantioselectivities ranging from poor to excellent. Aromatic aldehydes performed well, whereas aliphatic aldehydes gave lower ee values. The main advantages of this method are the low catalyst loading (1 mol%) and room temperature reactivity. Mechanistically, the reactive intermediate was shown to be a Pd(II) enolate, as determined by 1H NMR experiments.