Document Detail

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    
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.
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:  -    
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.
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