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Gold(III)-Catalyzed Intramolecular Furanylation and Cyclopropanation of Acyclic Conjugated Enynones
- Authors
- Oh, Chang Ho; Piao, Lanhua; Kim, Ji Hee
- Issue Date
- Jan-2013
- Publisher
- GEORG THIEME VERLAG KG
- Keywords
- cyclization; gold catalyst; furanylation; cyclopropanation; enynone
- Citation
- SYNTHESIS-STUTTGART, v.45, no.2, pp.174 - 182
- Indexed
- SCIE
SCOPUS
- Journal Title
- SYNTHESIS-STUTTGART
- Volume
- 45
- Number
- 2
- Start Page
- 174
- End Page
- 182
- ISSN
- 0039-7881
- 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.
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Related Researcher
- Oh, Chang Ho
- COLLEGE OF NATURAL SCIENCES (DEPARTMENT OF CHEMISTRY)