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Updated: Aug 9, 2025

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
A Stereospecific Alkene 1,2-Aminofunctionalization Platform for the Assembly of Complex Nitrogen-Containing Ring
Yuxiang Zhu1, Matthew J S Smith1, Wenbin Tu1,2
1Department of Chemistry, University of Liverpool, Crown Street, Liverpool, L69 7ZD, UK.
Abstract:
TFA promoted deprotection of O-Ts activated N-Boc hydroxylamines triggers aminofunctionalization-based polycyclizations of tethered alkenes. The processes involve intramolecular stereospecific aza-Prilezhaev alkene aziridination in advance of stereospecific C-N cleavage by a pendant nucleophile. Using this approach, a wide range of fully intramolecular alkene anti-1,2-difunctionalizations can be achieved, including diaminations, amino-oxygenations and amino-arylations. Trends associated with the regioselectivity of the C-N cleavage step are outlined. The method provides a broad and predictable platform for accessing diverse C(sp3 )-rich polyheterocycles of relevance to medicinal chemistry.
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