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

Joshua Farndon, Tom Young, John Bower

Research output: Contribution to journalArticle (Academic Journal)peer-review

9 Citations (Scopus)
189 Downloads (Pure)

Abstract

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.
Original languageEnglish
Pages (from-to)17846-17850
Number of pages5
JournalJournal of the American Chemical Society
Volume140
Issue number51
Early online date13 Dec 2018
DOIs
Publication statusPublished - 26 Dec 2018

Structured keywords

  • BCS and TECS CDTs

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