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Issue 17, 2010
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Metal-catalyzed transformations of propargylic alcohols into α,β-unsaturated carbonyl compounds: from the Meyer–Schuster and Rupe rearrangements to redox isomerizations

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Abstract

The catalytic isomerization of propargylic alcohols promoted by transition-metals represents a straightforward and appealing route to synthetically useful α,β-unsaturated carbonyl compounds. Three different reaction pathways are known for these atom-economical transformations: (i) the so-called Meyer–Schuster and Rupe rearrangements, in which a formal 1,3- or 1,2-shift of the hydroxyl group takes place, and (ii) the redox-type isomerization, which involves a simultaneous oxidation of the alcohol unit and reduction of the C[triple bond, length as m-dash]C bond. In this Perspective article an overview of the different metal catalysts presently available to promote these isomerization reactions, their mechanisms of action as well as relevant synthetic applications, is provided.

Graphical abstract: Metal-catalyzed transformations of propargylic alcohols into α,β-unsaturated carbonyl compounds: from the Meyer–Schuster and Rupe rearrangements to redox isomerizations

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Publication details

The article was received on 10 Nov 2009, accepted on 04 Jan 2010 and first published on 08 Feb 2010


Article type: Perspective
DOI: 10.1039/B923602C
Citation: Dalton Trans., 2010,39, 4015-4031
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    Metal-catalyzed transformations of propargylic alcohols into α,β-unsaturated carbonyl compounds: from the Meyer–Schuster and Rupe rearrangements to redox isomerizations

    V. Cadierno, P. Crochet, S. E. García-Garrido and J. Gimeno, Dalton Trans., 2010, 39, 4015
    DOI: 10.1039/B923602C

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