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Metal-catalyzed transformations of propargylic alcohols into alpha,beta-unsaturated carbonyl compounds: from the Meyer-Schuster and Rupe rearrangements to redox isomerizations.
MedLine Citation:
PMID:  20390164     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
The catalytic isomerization of propargylic alcohols promoted by transition-metals represents a straightforward and appealing route to synthetically useful alpha,beta-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]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.
Authors:
Victorio Cadierno; Pascale Crochet; Sergio E Garc?a-Garrido; Jos? Gimeno
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Publication Detail:
Type:  Journal Article     Date:  2010-02-08
Journal Detail:
Title:  Dalton transactions (Cambridge, England : 2003)     Volume:  39     ISSN:  1477-9234     ISO Abbreviation:  Dalton Trans     Publication Date:  2010 May 
Date Detail:
Created Date:  2010-04-14     Completed Date:  2010-06-29     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101176026     Medline TA:  Dalton Trans     Country:  England    
Other Details:
Languages:  eng     Pagination:  4015-31     Citation Subset:  -    
Affiliation:
Departamento de Qu?mica Org?nica e Inorg?nica, Instituto Universitario de Qu?mica Organomet?lica Enrique Moles (Unidad Asociada al CSIC), Universidad de Oviedo, Juli?n Claver?a 8, 33006, Oviedo, Spain. vcm@uniovi.es
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