Synthesis of spirocyclic enones by rhodium-catalyzed dearomatizing oxidative annulation of 2-alkenylphenols with alkynes and enynes
The dearomatizing oxidative annulation of 2-alkenylphenols with alkynes and enynes proceeds with high yields and regioselectivities under Rh(III) catalysis. These reactions are successful using Cu(OAc)2 or air as the stoichiometric oxidant, and provide spirocyclic enones, the basic ring system of wh...
| Main Authors: | , , , |
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| Format: | Article |
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Wiley-VCH Verlag
2014
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| Online Access: | https://eprints.nottingham.ac.uk/31657/ |
| _version_ | 1848794246950158336 |
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| author | Kujawa, Szymon Best, Daniel Burns, David J. Lam, Hon Wai |
| author_facet | Kujawa, Szymon Best, Daniel Burns, David J. Lam, Hon Wai |
| author_sort | Kujawa, Szymon |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | The dearomatizing oxidative annulation of 2-alkenylphenols with alkynes and enynes proceeds with high yields and regioselectivities under Rh(III) catalysis. These reactions are successful using Cu(OAc)2 or air as the stoichiometric oxidant, and provide spirocyclic enones, the basic ring system of which appears in several natural products. Application of this process to the preparation of a highly functionalized tetracycle is also demonstrated. |
| first_indexed | 2025-11-14T19:13:09Z |
| format | Article |
| id | nottingham-31657 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| last_indexed | 2025-11-14T19:13:09Z |
| publishDate | 2014 |
| publisher | Wiley-VCH Verlag |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-316572020-05-04T16:49:46Z https://eprints.nottingham.ac.uk/31657/ Synthesis of spirocyclic enones by rhodium-catalyzed dearomatizing oxidative annulation of 2-alkenylphenols with alkynes and enynes Kujawa, Szymon Best, Daniel Burns, David J. Lam, Hon Wai The dearomatizing oxidative annulation of 2-alkenylphenols with alkynes and enynes proceeds with high yields and regioselectivities under Rh(III) catalysis. These reactions are successful using Cu(OAc)2 or air as the stoichiometric oxidant, and provide spirocyclic enones, the basic ring system of which appears in several natural products. Application of this process to the preparation of a highly functionalized tetracycle is also demonstrated. Wiley-VCH Verlag 2014-06-06 Article PeerReviewed Kujawa, Szymon, Best, Daniel, Burns, David J. and Lam, Hon Wai (2014) Synthesis of spirocyclic enones by rhodium-catalyzed dearomatizing oxidative annulation of 2-alkenylphenols with alkynes and enynes. Chemistry - a European Journal, 20 (28). pp. 8599-8602. ISSN 0947-6539 http://onlinelibrary.wiley.com/doi/10.1002/chem.201403454/abstract doi:10.1002/chem.201403454 doi:10.1002/chem.201403454 |
| spellingShingle | Kujawa, Szymon Best, Daniel Burns, David J. Lam, Hon Wai Synthesis of spirocyclic enones by rhodium-catalyzed dearomatizing oxidative annulation of 2-alkenylphenols with alkynes and enynes |
| title | Synthesis of spirocyclic enones by rhodium-catalyzed dearomatizing oxidative annulation of 2-alkenylphenols with alkynes and enynes |
| title_full | Synthesis of spirocyclic enones by rhodium-catalyzed dearomatizing oxidative annulation of 2-alkenylphenols with alkynes and enynes |
| title_fullStr | Synthesis of spirocyclic enones by rhodium-catalyzed dearomatizing oxidative annulation of 2-alkenylphenols with alkynes and enynes |
| title_full_unstemmed | Synthesis of spirocyclic enones by rhodium-catalyzed dearomatizing oxidative annulation of 2-alkenylphenols with alkynes and enynes |
| title_short | Synthesis of spirocyclic enones by rhodium-catalyzed dearomatizing oxidative annulation of 2-alkenylphenols with alkynes and enynes |
| title_sort | synthesis of spirocyclic enones by rhodium-catalyzed dearomatizing oxidative annulation of 2-alkenylphenols with alkynes and enynes |
| url | https://eprints.nottingham.ac.uk/31657/ https://eprints.nottingham.ac.uk/31657/ https://eprints.nottingham.ac.uk/31657/ |