Premium
Gold( I )‐Catalyzed Intramolecular Cyclopropanation of Dienynes
Author(s) -
NietoOberhuber Cristina,
López Salomé,
Muñoz M. Paz,
JiménezNúñez Eloísa,
Buñuel Elena,
Cárdenas Diego J.,
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.200501089
Subject(s) - cyclopropanation , intramolecular force , catalysis , chemistry , combinatorial chemistry , stereochemistry , organic chemistry
Gold( I ) complexes are the most active catalysts for the biscyclopropanation of dienynes to form tetracyclic compounds. Pt II and Zn II are also able to promote the biscyclopropanation, although less efficiently. The configurations obtained in all cases with the use of gold( I ) catalysts can be explained by the pathway proceeding through anti cyclopropyl gold carbenes. Similar intermediates are most probably involved in reactions catalyzed by Ru II and Pt II . Two different cyclopropanation pathways have been found; they depend on the structures of the cyclopropyl gold carbenes ( anti or syn ) and the relative arrangements of the metal carbenes and the alkenes.