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Synthesis 2017; 49(19): 4461-4468
DOI: 10.1055/s-0036-1590885
DOI: 10.1055/s-0036-1590885
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Synthesis of Functionalized Cyclopentene Derivatives through Gold-Catalyzed Reaction of Stabilized Vinyldiazo Compounds and Styrenes
The authors thank the Ministerio de Economía y Competitividad (MINECO, grant CTQ2013-41511-P), Agencia Estatal de Investigación (AEI) and Fondo Europeo de Desarrollo Regional (FEDER) (grant CTQ2016–76840-R), and Principado de Asturias (grant GRUPIN14–013 and predoctoral grant to E. L.).Further Information
Publication History
Received: 28 June 2017
Accepted after revision: 27 July 2017
Publication Date:
23 August 2017 (online)


Abstract
The reaction of alkenyldiazo compounds with styrene derivatives in the presence of [Au(IPr)(MeCN)][SbF6] provided cyclopentene derivatives resulting from a formal [3+2] cycloaddition reaction as major products. This reaction outcome stands in marked contrast to that previously observed for other olefinic derivatives. From a mechanistic point of view, this process would involve the initial generation of a highly electrophilic alkenylgold carbene intermediate, which would be subsequently involved in a stepwise carbocationic process.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1590885.
- Supporting Information