Bench‐Stable α‐Fluoroamines: Synthesis, Properties, and Application in Medicinal Chemistry
ABSTRACT Aliphatic N ‐unprotected α‐fluoroamines are unstable due to dehydrofluorination. Here, we show that the incorporation of the CH 2 ‐group into the elusive α‐fluoropiperidine provides a stable α‐fluoroamine with the 2‐azabicyclo[2.2.1]heptane core. The latter does not eliminate HF because of Bredt's rule. The high stability of this α‐fluoroamine allows its wide chemical modifications and use in medicinal chemistry.
Authors
- Iryna V. Sadkova
- Pavel K. Mykhailiuk (ORCID: https://orcid.org/0000-0003-1821-9011)
- Vadym V. Levterov
- Henry S. Rzepa (ORCID: https://orcid.org/0000-0002-8635-8390)
- Oleh V. Shablykin (ORCID: https://orcid.org/0000-0001-6810-9860)
- Petro Borysko (ORCID: https://orcid.org/0000-0002-5840-5233)
- Oleksandr Stashkevych
- Volodymyr Kokhalskyi
- Vadym Konashuk
- Olha Shevchuk
Institutions
- Taras Shevchenko National University of Kyiv (UA)
- Institute of Bioorganic Chemistry and Petrochemistry V.P. Kukhar (UA)
- Imperial College London (GB)
- Enamine (Ukraine) (UA)
Publication Details
- Journal
- Angewandte Chemie
- Published
- 2026-10-06
- DOI
- https://doi.org/10.1002/ange.5080799
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00