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

Nucleophilic organic base DABCO (1,4-diazabicyclo[2.2.2]octane)-mediated Meinwald rearrangement of various epoxides was investigated. 2-Aryl-, alkenyl-, and alkynylepoxides generate the corresponding methyl ketones chemospecifically in good to excellent yields. The current DABCO-mediated Meinwald rearrangement of epoxides features readily accessible starting materials, a wide substrate scope, a transition-metal- and acid-free environment, and chemospecificity in the isomerization of epoxides.