Sequential Morita–Baylis–Hillman/Achmatowicz reactions: an expeditious access to pyran-3(6H)-ones with a unique substitution pattern

Abstract

We herein disclosed a novel approach to synthesize densely functionalized 6-hydroxy-2H-pyran-3(6H)-ones with moderate to good diastereoselectivity. The method is based on a two step sequence using Morita-Baylis-Hillman adducts as substrates for the Achmatowicz rearrangement, allowing the preparation of highly substituted pyran-3-ones with overall yields ranging from 17% to 80% and a unique substitution pattern