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Synfacts 2010(7): 0802-0802
DOI: 10.1055/s-0029-1220077
DOI: 10.1055/s-0029-1220077
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Nickel-Catalyzed Asymmetric Hydroalkynylation of 1,3-Dienes
M. Shirakura, M. Suginome*
Kyoto University, Japan
Further Information
Publication History
Publication Date:
22 June 2010 (online)
Significance
Catalytic conversion of alkyne C-H bonds through C-C bond formation without the stoichiometric generation of acetylides is a desirable atom-economical process. The catalytic hydroalkynylation (addition of alkyne C-H bonds across unactivated C-C multiple bonds) has gained significant attention, but the asymmetric version of such process has been limited to rhodium-catalyzed hydroalkynylation of allenes. The authors report a nickel-catalyzed asymmetric hydroalkynylation of 1-aryl-1,3-butadienes 2 with a terminal alkyne 1 that contains an α-siloxy-sec-alkyl group, in the presence of a TADDOL-based chiral phosphoramidite ligand (R,R)-L.