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Stereospecific Alkene Aziridination Using a Bifunctional Amino-Reagent: An Aza-Prilezhaev Reaction

Research output: Contribution to journalArticle

Original languageEnglish
Pages (from-to)17846-17850
Number of pages5
JournalJournal of the American Chemical Society
Issue number51
Early online date13 Dec 2018
DateAccepted/In press - 7 Dec 2018
DateE-pub ahead of print - 13 Dec 2018
DatePublished (current) - 26 Dec 2018


In situ deprotection (TFA) of O-Ts activated N-Boc hydroxylamines triggers intramolecular aziridination of N-tethered alkenes to provide complex N-heterocyclic ring systems. Synthetic and computational studies corroborate a diastereospecific aza-Prilezhaev-type mechanism. The feasibility of related intermolecular alkene aziridinations is also demonstrated.

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