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Gold- and Brønsted Acid-Catalyzed Cycloisomerization of 1,8-Diynyl Vinyl Acetates to Bicyclo[2.2.1]hept-2-en-7-ones
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Chen, Xiaoyu, Day, David Philip, Teo, Wan Teng and Chan, Philip Wai Hong (2016) Gold- and Brønsted Acid-Catalyzed Cycloisomerization of 1,8-Diynyl Vinyl Acetates to Bicyclo[2.2.1]hept-2-en-7-ones. Organic Letters, 18 (22). pp. 5936-5939. doi:10.1021/acs.orglett.6b03049 ISSN 1523-7060.
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Official URL: http://dx.doi.org/10.1021/acs.orglett.6b03049
Abstract
A synthetic method for the efficient assembly of bicyclo[2.2.1]hept-2-en-7-ones that relies on gold(I)-catalyzed Rautenstrauch rearrangement followed by Brønsted acid-mediated formal [3 + 2]-cycloaddition/deacetylation of 1,8-diynyl vinyl acetates at room temperature under atmospheric conditions is described.
| Item Type: | Journal Article | ||||||||
|---|---|---|---|---|---|---|---|---|---|
| Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||||||
| Journal or Publication Title: | Organic Letters | ||||||||
| Publisher: | American Chemical Society | ||||||||
| ISSN: | 1523-7060 | ||||||||
| Official Date: | 18 November 2016 | ||||||||
| Dates: |
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| Volume: | 18 | ||||||||
| Number: | 22 | ||||||||
| Page Range: | pp. 5936-5939 | ||||||||
| DOI: | 10.1021/acs.orglett.6b03049 | ||||||||
| Status: | Peer Reviewed | ||||||||
| Publication Status: | Published | ||||||||
| Access rights to Published version: | Restricted or Subscription Access |
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