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Nucleophilic Organic Base DABCO-Mediated Chemospecific Meinwald Rearrangement of Terminal Epoxides into Methyl Ketones

Siqi Li, Yi Shi, Pingfan Li*, Jiaxi Xu*

*Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing 100029, People’s Republic of China, Email: lipfmail.buct.edu.cn, jxxumail.buct.edu.cn

S. Li, Y. Shi, P. Li, J. Xu, J. Org. Chem., 2019, 84, 4443-4450.

DOI: 10.1021/acs.joc.8b03171 (free Supporting Information)


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Abstract

DABCO-mediated Meinwald rearrangements of 2-aryl-, alkenyl-, and alkynylepoxides provide the corresponding methyl ketones chemospecifically in good yields. The reaction offers readily accessible starting materials, a wide substrate scope, a transition-metal- and acid-free environment, and chemospecificity in the isomerization of epoxides.

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Key Words

enones, ketones


ID: J42-Y2019