BF3·OEt2-mediated syn-selective Meyer–Schuster rearrangement of phenoxy propargyl alcohols for Z-β-aryl-α,β-unsaturated esters

Abstract

Synthesis of Z-β-aryl-α,β-unsaturated esters from readily available 1-aryl-3-phenoxy propargyl alcohols is achieved via a BF₃-mediated syn-selective Meyer–Schuster rearrangement under ambient conditions. The reaction mechanism is postulated to involve an electrophilic borylation of an allene intermediate as the key step to kinetically control the stereoselectivity.