Synthesis of spirocyclic enones by rhodium-catalyzed dearomatizing oxidative annulation of 2-alkenylphenols with alkynes and enynes

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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

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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/chem.201403454/abstract

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.

Item Type:

Article

RIS ID:

https://nottingham-repository.worktribe.com/output/731037

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.wiley.com/doi/10.1002/chem.201403454/abstract. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.

Schools/Departments:

University of Nottingham, UK > Faculty of Science > School of Chemistry

Identification Number:

https://doi.org/10.1002/chem.201403454

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