Issue 29, 2016

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
18 May 2016
Accepted
21 Jun 2016
First published
22 Jun 2016

Org. Biomol. Chem., 2016,14, 7001-7009

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

S. Puri, M. Hari Babu and M. Sridhar Reddy, Org. Biomol. Chem., 2016, 14, 7001 DOI: 10.1039/C6OB01090C

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