Gold-catalysed rearrangement of unconventional cyclopropane-tethered 1,5-enynes

Rubén Vicente; Eva Tudela; Miguel A. Rodríguez; Ángel L. Suárez-Sobrino; Alfredo Ballesteros

doi:10.1039/D2CC02869G

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Gold-catalysed rearrangement of unconventional cyclopropane-tethered 1,5-enynes†

Rubén Vicente,

*^a Eva Tudela,^a Miguel A. Rodríguez,^b Ángel L. Suárez-Sobrino^a and Alfredo Ballesteros

*^a

Author affiliations

* Corresponding authors

^a Departamento de Química Orgánica e Inorgánica and Instituto Universitario de Química Organometálica “Enrique Moles”, Universidad de Oviedo C/Julian Clavería 8, Oviedo, Spain
E-mail: vicenteruben@uniovi.es

^b Departamento de Química, Centro de Investigación en Síntesis Química, Universidad de la Rioja, Logroño, Spain

Abstract

The synthesis of particular cyclopropane-tethered 1,5-enynes, namely 6-alkynyl-4-alkylidenebicyclo[3.1.0]hex-2-enes, enabled the discovery of unprecedented gold-catalyzed rearrangment to indenes. A computational study of the mechanism of this profound skeleton rearrangement is also disclosed.

This article is part of the themed collection: 2022 Pioneering Investigators

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DOI: https://doi.org/10.1039/D2CC02869G
Article type: Communication
Submitted: 20 Maijs 2022
Accepted: 22 Jūn. 2022
First published: 22 Jūn. 2022

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Chem. Commun., 2022,58, 8206-8209

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Gold-catalysed rearrangement of unconventional cyclopropane-tethered 1,5-enynes

R. Vicente, E. Tudela, M. A. Rodríguez, Á. L. Suárez-Sobrino and A. Ballesteros, Chem. Commun., 2022, 58, 8206 DOI: 10.1039/D2CC02869G

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Chemical Communications

Gold-catalysed rearrangement of unconventional cyclopropane-tethered 1,5-enynes†

Abstract

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Gold-catalysed rearrangement of unconventional cyclopropane-tethered 1,5-enynes

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