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Updated: Jun 27, 2026

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Radical cascades using enantioenriched 7-azabenzonorbornenes and their applications in synthesis
David M Hodgson1, Leonard H Winning
1Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK. david.hodgson@chem.ox.ac.uk
Abstract:
Tandem deoxygenation-neophyl-type radical rearrangement-electrophile trapping using xanthates from 7-azabenzonorbornadienes gives 3-exo-substituted 2-aza-5,6-benzonorbornenes, which in some cases undergo isomerisation to (aminomethyl)indenes. The starting xanthates are accessible in good yields and high enantiomeric ratios via asymmetric hydroboration of (aryne/pyrrole-derived) 7-azabenzonorbornadienes. Oxidation (using RuO(4)) and Birch reduction of the 2-aza-5,6-benzonorbornenes provide access to substituted pyrrolidines and tetrahydroindenes, respectively.
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