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

The Journal of Organic Chemistry
Siqi LiJiaxi Xu

Abstract

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.

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Citations

Oct 1, 2019·Chemical Communications : Chem Comm·Naama Karton-LifshinYossi Zafrani
Dec 6, 2019·Organic & Biomolecular Chemistry·Chuangchuang Xu, Jiaxi Xu
Jan 29, 2020·The Journal of Organic Chemistry·Yong-Liang SuMichael P Doyle

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