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Synthesis 2013; 45(2): 174-182
DOI: 10.1055/s-0032-1317926
DOI: 10.1055/s-0032-1317926
paper
Gold(III)-Catalyzed Intramolecular Furanylation and Cyclopropanation of Acyclic Conjugated Enynones
Further Information
Publication History
Received: 19 September 2012
Accepted after revision: 23 November 2012
Publication Date:
13 December 2012 (online)
Abstract
We have developed an efficient cascade gold-catalyzed furanylation–cyclopropanation of acyclic (E)-deca-2,9-dien-4-yn-1-ones and an (E)-undeca-2,10-dien-4-yn-1-one to give 1-(2-furyl)bicyclo[3.1.0]hexanes and a 1-(2-furyl)bicyclo[4.1.0]heptane, respectively. This requires a configurational change from the E-isomer to the Z-isomer prior to furan formation. The intermediate was proposed to be a gold–carbene, which would undergo cyclopropanation to furnish the product.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
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