Catalytic Enantioselective Inverse-Electron-Demand Diels–Alder Reaction of 2-Pyrones and Vinyl Selenides

Abstract

We report herein an asymmetric inverse-electron-demand Diels–Alder (IEDDA) reaction of electron-deficient 2-pyrones with various phenyl vinyl selenides catalyzed by a chiral bis(oxazoline)/Cu(OTf)2 complex. Using a side arm-modified chiral bis(oxazoline)ligand, a variety of [2,2,2]-bicyclic lactones with phenyl selenide substituents were obtained with good to excellent yields (up to 99% yield) and enantioselectivities (up to 98% ee) under mild conditions. Based on this strategy, enantioselective synthesis of Corey lactone was accomplished in a highly concise manner.