Isoxazolidines are interesting heterocyclic motifs due to their valuable biological activities as well as their synthetic utility. Alkene difunctionalization is an important strategy for isoxazolidine synthesis. Our lab has developed the alkene diamination reaction using Earth-abundant copper salts for the synthesis of a range of heterocycles including indolines, pyrrolidines, furans and benzodiazepinone. Herein, we report the first alkene diamination reaction that enables isoxazolidine ring synthesis. This reaction also demonstrates unsaturated carbamates as good copper-catalyzed diamination substrates for the first time. The external amine scope includes sulfonamides, anilines, benzamide and morpholine. Reductive N-O bond cleavage to give the corresponding diamino alcohols, which are important synthetically useful and biologically active motifs, was also demonstrated.

Stereoselective synthesis of isoxazolidines <i>via</i> copper-catalyzed alkene diamination

253rd National Meeting (2017)

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Stereoselective synthesis of isoxazolidines via copper-catalyzed alkene diamination