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Gold-catalyzed tandem 1,3-migration/double cyclopropanation of 1-Ene-4,n-diyne esters to tetracyclodecene and tetracycloundecene derivatives
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Chen, Cuili, Zou, Yongzhen, Chen, Xianxiao, Zhang, Xiaoxiang, Rao, Weidong and Chan, Philip Wai Hong (2016) Gold-catalyzed tandem 1,3-migration/double cyclopropanation of 1-Ene-4,n-diyne esters to tetracyclodecene and tetracycloundecene derivatives. Organic Letters, 18 (18). pp. 4730-4733. doi:10.1021/acs.orglett.6b02404 ISSN 1523-7060.
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Official URL: http://dx.doi.org/10.1021/acs.orglett.6b02404
Abstract
A synthetic method that relies on Au(I)-catalyzed tandem 1,3-acyloxy migration/double cyclopropanation of 1-ene-4,9-diyne and 1-ene-4,10-diyne esters to construct the respective architecturally challenging tetracyclodecene and tetracycloundecene derivatives is described. Achieved under mild reaction conditions, the transformation was shown to be robust with a wide variety of substitution patterns tolerated to give the two members of the carbocyclic family in good to excellent yields and as a single regio- and diastereomer.
Item Type: | Journal Article | ||||||||
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Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||||||
Journal or Publication Title: | Organic Letters | ||||||||
Publisher: | American Chemical Society | ||||||||
ISSN: | 1523-7060 | ||||||||
Official Date: | 16 September 2016 | ||||||||
Dates: |
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Volume: | 18 | ||||||||
Number: | 18 | ||||||||
Page Range: | pp. 4730-4733 | ||||||||
DOI: | 10.1021/acs.orglett.6b02404 | ||||||||
Status: | Peer Reviewed | ||||||||
Publication Status: | Published | ||||||||
Access rights to Published version: | Restricted or Subscription Access |
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