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Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids
Published on: June 28, 2019
Chemoselective P(NMe2)3-Mediated Reductive Epoxidation between Two Different Carbonyl Electrophiles: Synthesis of
Rong Zhou1, Honghui Zhang1, Jialin Liu1
1College of Chemistry and Chemical Engineering , Taiyuan University of Technology , Taiyuan 030024 , P. R. China.
Abstract:
Herein, we report a chemoselective P(NMe2)3-mediated reductive epoxidation of α-dicarbonyl compounds such as isatins, α-keto esters, and α-diketones with aldehydes and ketones, leading to an efficient synthesis of a wide range of highly functionalized unsymmetrical epoxides in moderate to excellent yields and diastereoselectivities. The Kukhtin-Ramirez adduct, which is exclusively generated in situ from an α-dicarbonyl compound and P(NMe2)3, plays a key role in governing the chemoselectivity. It represents the first practical synthesis of unsymmetrical epoxides via direct reductive epoxidation of two different carbonyl electrophiles and also complements the existing methods of generating epoxides.
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