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Alkene oxyamination using malonoyl peroxides : preparation of pyrrolidines and isoxazolidines

Alamillo-Ferrer, Carla and Curle, Jonathan M and Davidson, Stuart C and Lucas, Simon C C and Atkinson, Stephen J and Campbell, Matthew and Kennedy, Alan R and Tomkinson, Nicholas C O (2018) Alkene oxyamination using malonoyl peroxides : preparation of pyrrolidines and isoxazolidines. Journal of Organic Chemistry, 83 (12). pp. 6728-6740. ISSN 0022-3263

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    Treatment of homoallylic N-tosyl amines or allylic N-tosyl hydroxylamines with 1.5 equiv of a malonoyl peroxide provides a stereoselective method to access functionalized pyrrolidines and isoxazolidines. This metal free alkene oxyamination proceeds in 50-85% yield and up to 13:1 trans-selectivity. In addition, the relative stereochemistry of the oxygen and nitrogen substituents can be inverted through an oxidation/reduction sequence or inverting the stereochemistry of the starting alkene. Mechanistic investigations show a higher reactivity for hydroxyl nucleophiles over sulfonamide nucleophiles revealing a preference for dioxygenation over oxyamination.