Gold( I )‐Catalyzed Cyclizations of 1,6‐Enynes: Alkoxycyclizations and  exo / endo  Skeletal Rearrangements | Zendy

NietoOberhuber Cristina | Zendy; Muñoz M. Paz | Zendy; López Salomé | Zendy; JiménezNúñez Eloísa | Zendy; Nevado Cristina | Zendy; HerreroGómez Elena | Zendy; Raducan Mihai | Zendy; Echavarren Antonio M. | Zendy

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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.

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