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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

Authors

Szymon Kujawa

Daniel Best

David J. Burns

HON LAM Hon.Lam@nottingham.ac.uk
Professor of Sustainable Chemistry



Abstract

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.

Citation

Kujawa, S., Best, D., Burns, D. J., & Lam, H. W. (2014). Synthesis of spirocyclic enones by rhodium-catalyzed dearomatizing oxidative annulation of 2-alkenylphenols with alkynes and enynes. Chemistry - A European Journal, 20(28), doi:10.1002/chem.201403454

Journal Article Type Article
Publication Date Jun 6, 2014
Deposit Date Feb 12, 2016
Publicly Available Date Feb 12, 2016
Journal Chemistry - a European Journal
Print ISSN 0947-6539
Electronic ISSN 0947-6539
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 20
Issue 28
DOI https://doi.org/10.1002/chem.201403454
Public URL http://eprints.nottingham.ac.uk/id/eprint/31657
Publisher URL http://onlinelibrary.wiley.com/doi/10.1002/chem.201403454/abstract
Related Public URLs http://www.interscience.wiley.com/
Copyright Statement Copyright information regarding this work can be found at the following address: http://eprints.nottingh.../end_user_agreement.pdf
Additional Information This is the peer reviewed version of the following article: Kujawa, S., Best, D., Burns, D. J. and Lam, H. W. (2014), Synthesis of Spirocyclic Enones by Rhodium-Catalyzed Dearomatizing Oxidative Annulation of 2-Alkenylphenols with Alkynes and Enynes. Chem. Eur. J., 20: 8599–8602. doi:10.1002/chem.201403454, which has been published in final form at http://onlinelibrary.wi...hem.201403454/abstract. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.

Files

HWL SzymonDanDave Rh-Catalyzed Dearomatizing Spiroannulation CEJ submission.pdf (754 Kb)
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Copyright Statement
Copyright information regarding this work can be found at the following address: http://eprints.nottingham.ac.uk/end_user_agreement.pdf





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