Copper(H) triflate-catalyzed nucleophilic substitution of propargylic acetates with enoxysilanes. A straightforward synthetic route to polysubstituted furans

Abstract

A novel and efficient procedure for the synthesis of gamma-alkynyl ketones by the nucleophilic substitution of propargylic acetates with enoxysilanes in the presence of a catalytic amount of Copper(II) triflate, has been developed. The substitution reaction can be followed by a 4-toluenesulfonic acid-catalyzed cyclization without purification of the gamma-alkynyl ketone intermediates, offering a straightforward synthetic route to polysubstituted furans.