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Cycloisomerization of 1, n ‐Enynes: Challenging Metal‐Catalyzed Rearrangements and Mechanistic Insights
Author(s) -
Michelet Véronique,
Toullec Patrick Y.,
Genêt JeanPierre
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200701589
Subject(s) - cycloisomerization , enyne , catalysis , intramolecular force , atom economy , chemistry , intermolecular force , tandem , isomerization , combinatorial chemistry , stereochemistry , molecule , organic chemistry , materials science , composite material
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.