title: 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.
authors.affiliation: Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, BS-10/1, Sector 10, Jankipuram extension, Sitapur Road, Lucknow 226031, India. msreddy@cdri.res.in.
authors.forename: Surendra
authors.initials: S
authors.lastname: Puri
authors.forename: Madala
authors.initials: M
authors.lastname: Hari Babu
authors.forename: Maddi
authors.initials: M
authors.lastname: Sridhar Reddy