Bis-zirconocenes Generatedfrom Weinreb 2‑Allylaminoacetamidesas 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.

Publication Details

Journal
Figshare
Published
2025-03-14
DOI
https://doi.org/10.1021/acs.joc.4c02399.s001
Primary Topic
Advanced Synthetic Organic Chemistry
Type
article
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article

Bis-zirconocenes Generatedfrom Weinreb 2‑Allylaminoacetamidesas Key Intermediates for a Diastereoselective Approach to 2- and 6‑Substituted-3-Aminopiperidines

Figshare
Advanced Synthetic Organic Chemistry
article

Bis-zirconocenes Generatedfrom Weinreb 2‑Allylaminoacetamidesas Key Intermediates for a Diastereoselective Approach to 2- and 6‑Substituted-3-Aminopiperidines

article en

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 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.

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Advanced Synthetic Organic Chemistry
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Bis-zirconocenes Generatedfrom Weinreb 2‑Allylaminoacetamidesas Key Intermediates for a Diastereoselective Approach to 2- and 6‑Substituted-3-Aminopiperidines · Figshare (2025) | TGRS Research Map | TGRS