Scandium-catalyzed asymmetric addition of allenylsilanes to β,γ-unsaturated α-ketoesters: enantioselective synthesis of tertiary homopropargylic allylic alcohols

Abstract

An efficient scandium catalyzed regio- and enantioselective 1,2-homopropargylic addition of β,γ-unsaturated α-ketoesters with 1-substituted allenylsilanes has been developed. This protocol enables the synthesis of a broad range of enantioenriched tertiary homopropargylic allylic alcohols in good yields with excellent enantioselectivities. The practicality of the method was further demonstrated through gram-scale reactions and versatile synthetic transformations of the product.