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Org Biomol Chem. 2009 Oct 21;7(20):4149-58. doi: 10.1039/b912099h. Epub 2009 Sep 14.

The Meyer-Schuster rearrangement for the synthesis of alpha,beta-unsaturated carbonyl compounds.

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Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL, USA.


The Meyer-Schuster rearrangement is the conversion of propargyl alcohols into alpha,beta-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 alpha,beta-unsaturated carbonyl compounds as part of a two-stage olefination strategy.

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