The Meyer–Schuster rearrangement for the synthesis of α,β-unsaturated carbonyl compounds

Organic & Biomolecular Chemistry Pub Date: 2009-09-14 DOI: 10.1039/B912099H

Abstract

The Meyer–Schuster rearrangement is the conversion of propargyl alcohols into α,β-unsaturated carbonyl compounds via a formal 1,3-hydroxyl shift and tautomerization. The major challenge associated with the Meyer–Schuster reaction is that of selectively promoting the desired rearrangement over the myriad other reaction pathways available to propargyl alcohols. This Perspective Article features recent advances in the Meyer–Schuster reaction, including several demonstrated techniques for improving the scope. Strengths and weaknesses of each technique are discussed, and outstanding problems that warrant further study are highlighted. The primary motivation for research and development of the Meyer–Schuster rearrangement is as a means of preparing α,β-unsaturated carbonyl compounds as part of a two-stage olefination strategy.

Graphical abstract: The Meyer–Schuster rearrangement for the synthesis of α,β-unsaturated carbonyl compounds
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