Oxovanadium-Mediated Asymmetric Alkynyl Additions to Aldehydes

Significance

Since the first report on asymmetric alkynyl addition to aldehydes by Corey et al. (J. Am. Chem. Soc. 1994, 116, 3151-3152), most recent publications have focused on the use of zinc (for a leading example, see: D. E. Frantz, R. Fässler, E. M. Carreira J. Am. Chem. Soc. 2000, 122, 1806-1807) or titanium reagents (X. Li, G. Lu, W. H. Kwok, A. S. C. Chan J. Am. Chem. Soc. 2002, 124, 12636-12637). In the present paper the authors describe the first examples of the use of an oxovanadium(V) complex to mediate this reaction. Enantioenriched propargyl alcohols are obtained in good to excellent yields.