Gold(I)-Catalyzed Cyclizations of 1,6-Enynes: Alkoxycyclizations andexo/endo Skeletal Rearrangements

Cristina Nieto-Oberhuber, Maria Munoz-Herranz, Salomé López, Eloísa Jiménez-Núñez, Cristina Nevado, Elena Herrero-Gómez, Mihai Raducan, Antonio M. Echavarren

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318 Citations (Scopus)

Abstract

Gold(I) complexes are the most active catalysts for the biscyclopropanation of dienynes to form tetracyclic compounds. PtII and ZnII 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 RuII and PtII. 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.
Original languageEnglish
Pages (from-to)1677-1693
Number of pages17
JournalChemistry - A European Journal
Volume12
Issue number6
DOIs
Publication statusPublished - 2006

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