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

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), https://doi.org/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: 1521-3765
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 20
• Issue: 28
• DOI: https://doi.org/10.1002/chem.201403454
• Public URL: https://nottingham-repository.worktribe.com/output/731037
• Publisher URL: http://onlinelibrary.wiley.com/doi/10.1002/chem.201403454/abstract
• Related Public URLs: http://www.interscience.wiley.com/
• 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.