Bis-zirconocenes Generated from Weinreb 2-Allylaminoacetamides as Key Intermediates for a Diastereoselective Approach to 2- and 6-Substituted-3-Aminopiperidines
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 BF<sub>3</sub>-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.
Authors
- Jean‐Bernard Behr (ORCID: https://orcid.org/0000-0002-8998-8806)
- Jean‐Luc Vasse (ORCID: https://orcid.org/0000-0003-0802-1095)
- Christelle Kowandy (ORCID: https://orcid.org/0000-0002-3276-0763)
- Aurélien Coelho
- Mohamed El Gharbi
- Emilie Bianchi
Institutions
- International Council on Mining and Metals (GB)
- REGARDS Recherches en Économie Gestion AgroRessources Durabilité Santé (FR)
- Université de Reims Champagne-Ardenne (FR)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-03-14
- DOI
- https://doi.org/10.1021/acs.joc.4c02399
- Primary Topic
- Advanced Synthetic Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Centre National de la Recherche Scientifique
- Université de Reims Champagne-Ardenne