Journal of the American Chemical Society, Vol.133, No.27, 10332-10335, 2011
A General Copper-BINAP-Catalyzed Asymmetric Propargylation of Ketones with Propargyl Boronates
An operationally simple copper-BINAP-catalyzed, highly enantioselective propargylation of ketones is presented. The methodology was developed as an enantioselective process for methyl ethyl ketone and shown to be applicable to a wide variety of prochiral ketones. The resulting homopropargyl adducts are versatile latent carbonyls from which gamma-butyrolactones, beta-hydroxy methyl ketones, and beta-hydroxycarboxylates are readily obtained.