Issue 20, 2009
From the journal:

Organic & Biomolecular Chemistry

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

Douglas A. Engela  and  Gregory B. Dudley*a  

* Corresponding authors

a Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL, USA
E-mail: gdudley@chem.fsu.edu
Fax: +1-850-644-8281
Tel: +1-850-644-2333

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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Article information

DOI
https://doi.org/10.1039/B912099H
Article type
Perspective
Submitted
23 Jun 2009
Accepted
07 Aug 2009
First published
14 Sep 2009

Org. Biomol. Chem., 2009,7, 4149-4158

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

D. A. Engel and G. B. Dudley, Org. Biomol. Chem., 2009, 7, 4149 DOI: 10.1039/B912099H

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