Synthesis 2013; 45(2): 174-182
DOI: 10.1055/s-0032-1317926
paper
© Georg Thieme Verlag Stuttgart · New York

Gold(III)-Catalyzed Intramolecular Furanylation and Cyclopropanation of Acyclic Conjugated Enynones

Chang Ho Oh*
Department of Chemistry and Research Institute for Natural Science, Hanyang University, Sungdong-Gu, Seoul 133 791, South Korea   Fax: +82(2)22990762   Email: changho@hanyang.ac.kr
,
Lanhua Piao
Department of Chemistry and Research Institute for Natural Science, Hanyang University, Sungdong-Gu, Seoul 133 791, South Korea   Fax: +82(2)22990762   Email: changho@hanyang.ac.kr
,
Ji Hee Kim
Department of Chemistry and Research Institute for Natural Science, Hanyang University, Sungdong-Gu, Seoul 133 791, South Korea   Fax: +82(2)22990762   Email: changho@hanyang.ac.kr
› Author Affiliations
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

 
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