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Synfacts 2006(1): 0041-0041
DOI: 10.1055/s-2005-921670
DOI: 10.1055/s-2005-921670
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Asymmetric Propargyl Alcohols via Aldehyde Alkynylation
R. Takita, K. Yakura, T. Oshima, M. Shibasaki*
University of Tokyo, Japan
Further Information
Publication History
Publication Date:
16 December 2005 (online)
Significance
The alkynylation of aldehydes often requires the use of stoichiometric amounts of metallic reagents to ensure the alkyne nucleophilicity. This report presents a catalytic enantioselective method for the synthesis of propargyl alcohols via aldehyde alkynylation. The air stable, In(III)-BINOL complex promotes the addition of various alkynes to aliphatic, aromatic and heteroaromatic aldehydes with no observed Cannizaro-type side products.