Issue 30, 2012
From the journal:

Organic & Biomolecular Chemistry

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

Ana Escribano-Cuesta,a   Patricia Pérez-Galán,a   Elena Herrero-Gómez,a   Masaki Sekine,a   Ataualpa A. C. Braga,a   Feliu Maserasab  and  Antonio M. Echavarren*ac  

* Corresponding authors

a Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona, Spain
E-mail: aechavarren@iciq.es

b Departament de Química, Universitat Autónoma, de Barcelona, 08193 Bellaterra, Spain

c Departament de Química Analítica i Química Orgànica, Universitat Rovira i Virgili, C/Marcelli Domingo s/n, 43007 Tarragona, Spain

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.

Graphical abstract: The role of cyclobutenes in gold(i)-catalysed skeletal rearrangement of 1,6-enynes

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Article information

DOI
https://doi.org/10.1039/C2OB25419K
Article type
Paper
Submitted
27 Feb 2012
Accepted
02 May 2012
First published
03 May 2012

Org. Biomol. Chem., 2012,10, 6105-6111

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

A. Escribano-Cuesta, P. Pérez-Galán, E. Herrero-Gómez, M. Sekine, A. A. C. Braga, F. Maseras and A. M. Echavarren, Org. Biomol. Chem., 2012, 10, 6105 DOI: 10.1039/C2OB25419K

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