The role of cyclobutenes in gold(I)-catalysed skeletal rearrangement of 1,6-enynes

Ana Escribano-Cuesta, Patricia Pérez-Galán, Elena Herrero-Gómez, Masaki Sekine, Ataualpa A.C. Braga, Feliu Maseras, Antonio M. Echavarren

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46 Citations (Scopus)

Abstract

1,6-Enynes with electron-donating substituents at the alkyne undergo gold(i)-catalysed single cleavage skeletal rearrangement, whereas substrates with electron-withdrawing substituents evolve selectively to double cleavage rearrangement. Theoretical calculations provide a qualitative rationale for these effects, and suggest that bicyclo[3.2.0]hept-5-enes are involved as intermediates. We provide the first X-ray structural evidence for the formation of a product of this class in a cycloisomerisation of a 1,6-enyne. © 2012 The Royal Society of Chemistry.
Original languageEnglish
Pages (from-to)6105-6111
JournalOrganic and Biomolecular Chemistry
Volume10
Issue number30
DOIs
Publication statusPublished - 14 Aug 2012

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