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Gold( I )‐Catalyzed Cyclizations of 1,6‐Enynes: Alkoxycyclizations and exo / endo Skeletal Rearrangements
Author(s) -
NietoOberhuber Cristina,
Muñoz M. Paz,
López Salomé,
JiménezNúñez Eloísa,
Nevado Cristina,
HerreroGómez Elena,
Raducan Mihai,
Echavarren Antonio M.
Publication year - 2006
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200501088
Subject(s) - catalysis , chemistry , intramolecular force , stereochemistry , catalytic cycle , medicinal chemistry , organic chemistry
Gold( I ) complexes are the most active catalysts for alkoxy‐ or hydroxycyclization and for skeletal rearrangement reactions of 1,6‐enynes. Intramolecular alkoxycyclizations also proceed efficiently in the presence of gold( I ) catalysts. The first examples of the skeletal rearrangement of enynes by the endocyclic cyclization pathway are also documented. Iron( III ) is also able to catalyze exo and endo skeletal rearrangements of 1,6‐enynes, although the scope of this transformation is more limited. The gold( I )‐catalyzed endocyclic cyclization proceeds by a mechanism different from those followed in the presence of Pd II , Hg II , or Rh I catalysts.