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Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids
Published on: June 28, 2019
Ultrafast Mechanochemical Epoxidation of Aldehydes and Ketones
Zhongye Huang1, Xinhan Liu1, KaKing Yan1
1School of Physical Science and Technology, ShanghaiTech University, Shanghai201210, China.
Abstract:
We report a mechanochemical Corey-Chaykovsky epoxidation that converts aldehydes and ketones to epoxides within minutes under an ambient atmosphere using sulfonium or sulfoxonium salts, KOH, and minimal liquid additives. The method accommodates a broad substrate scope, is readily scalable, and often enables simple extraction without chromatography. It further enables telescoped sulfonium generation-oxidation-epoxidation, tunable enone chemoselectivity, and direct conversion of imines to unstabilized aziridines. An unexpected dependence of reactivity on the ylide precursor halide reveals distinct mechanochemical reactivity from that under conventional solution-phase conditions.
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