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Synfacts 2013; 9(2): 0165
DOI: 10.1055/s-0032-1317975
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Cobalt-Mediated Asymmetric 1,6-Alkyne Addition to Conjugated Carbonyls

Contributor(s):
Mark Lautens
,
Harald Weinstabl
Sawano T, Ashouri A, Nishimura T, * Hayashi T. * Kyoto University, Japan and A*STAR, Singapore
Cobalt-Catalyzed Asymmetric 1,6-Addition of (Triisopropylsilyl)acetylene to α,β,γ,δ-Unsaturated Carbonyl Compounds.

J. Am. Chem. Soc. 2012;
134: 18936-18939
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Further Information

Publication History

Publication Date:
18 January 2013 (online)

 
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Key words

asymmetric addition - α,β,γ,δ-unsaturated compounds - Duphos - 1,6-addition

Significance

Asymmetric additions of acetylenes to conjugated π-systems have gained growing interest in recent years (Y. Watanabe et al. J. Org. Chem. 1985, 50, 565; M. Shirakura, M. Suginome Angew. Chem. Int. Ed. 2010, 49, 3827). Herein, a cobalt-catalyzed addition of TIPS-acetylene is described.


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Comment

The presented method allows the asymmetric addition of TIPS-acetylene to α,β,γ,δ-unsaturated carbonyl compounds with high regio- and enantioselectivity.


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