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Updated: May 22, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Bis-zirconocenes Generated from Weinreb 2-Allylaminoacetamides as Key Intermediates for a Diastereoselective Approach
Mohamed El Gharbi1, Emilie Bianchi1, Aurélien Coelho1
1ICMR, CNRS UMR 7312, Université de Reims Champagne-Ardenne, 51687 Reims Cedex 2, France.
Abstract:
The synthesis of 2- and 6-substituted-3-aminopiperidines from Weinreb amides containing an allylamino fragment is reported. Involving the simultaneous hydrozirconation of the C═C and the C═O bonds, the cyclization was promoted by the BF3-mediated generation of an iminium. Proven to be highly diastereoselective, the sequence can be applied to diversely substituted unsaturated Weinreb amides and valorized through the preparation of bicyclic heterocycles.
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