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Cycloisomerization of 1,n-enynes: challenging metal-catalyzed rearrangements and mechanistic insights.
MedLine Citation:
PMID:  18381724     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
Metal-catalyzed cycloisomerization reactions of 1,n-enynes have appeared as conceptually and chemically highly attractive processes as they contribute to the highly demanded search for atom economy and allow the discovery of new reactions. Since the pioneering studies with palladium by the research group of Barry Trost in the mid-1980s, several other metals have been identified as excellent catalysts for the rearrangement of enyne skeletons. Moreover, the behavior of 1,n-enynes may be influenced by other functional groups such as alcohols, aldehydes, ethers, alkenes, or alkynes, thus enhancing the molecular complexity of the synthesized products. Apart from the intrinsic rearrangements of 1,n-enynes, several tandem reactions incorporating intramolecular trapping agents or intermolecular partners have been discovered. This Review aims to highlight the main contributions in this field of catalysis and to propose and comment on the mechanistic insights of the recent discoveries.
Authors:
Véronique Michelet; Patrick Y Toullec; Jean-Pierre Genêt
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Angewandte Chemie (International ed. in English)     Volume:  47     ISSN:  1521-3773     ISO Abbreviation:  Angew. Chem. Int. Ed. Engl.     Publication Date:  2008  
Date Detail:
Created Date:  2008-05-26     Completed Date:  2008-07-10     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0370543     Medline TA:  Angew Chem Int Ed Engl     Country:  Germany    
Other Details:
Languages:  eng     Pagination:  4268-315     Citation Subset:  -    
Affiliation:
Laboratoire de Synthèse Sélective Organique et Produits Naturels, UMR 7573, Ecole Nationale Supérieure de Chimie de Paris, 11, rue P. et M. Curie, 75231 Paris cedex 05, France. veronique-michelet@enscp.fr
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