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Synthesis of Cyclic Enones by Allyl-Palladium-Catalyzed α,β-Dehydrogenation

David Huang, Yizhou Zhao and Timothy R. Newhouse*

*Department of Chemistry, Yale University, 225 Prospect Street, New Haven, Connecticut 06520-8107, United States, Email: timothy.newhouseyale.edu

D. Huang, Y. Zhao, T. R. Newhouse, Org. Lett., 2018, 20, 684-687.

DOI: 10.1021/acs.orglett.7b03818 (free Supporting Information)


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Abstract

The use of allyl-palladium catalysis enables a one-step α,β-dehydrogenation of ketones via their zinc enolates. The optimized protocol utilizes commercially available Zn(TMP)2 as base and diethyl allyl phosphate as oxidant, operates under salt-free conditions, and tolerates a diverse scope of cycloalkanones.


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Key Words

cyclopentenones, cyclohexenones, diethyl allyl phosphate


ID: J54-Y2018