The atroposelective synthesis of barbiturate-substituted chiral styrenes

Abstract

Herein, the first report is made on the enantioselective synthesis of axially chiral barbiturate-substituted styrenes from vinylidene ortho-quinone methide (VQM) derived from 1-alkynylnaphthalen-2-ols and 5-substituted barbituric acids using a quinidine-based organocatalyst. This mild and straightforward protocol offers tolerance to a broad range of substrates bearing electronically diverse functional groups to afford axially chiral barbiturate-bearing styrenes in excellent yields (up to 99%) and diastereo- and enantioselectivities (up to 99%).