New Entries toward 3,3-Difluoropiperidines

Electrophilic substitution
DOI: 10.1021/jo800768q Publication Date: 2008-06-12T10:02:01Z
ABSTRACT
Difluoropiperidines attract considerable interest from organic and medicinal chemists, but their synthesis is often problematic. This paper describes a new synthetic pathway toward valuable 3,3-difluoropiperidines starting suitable δ-chloro-α,α-difluoroimines. The latter imines can be synthesized via electrophilic fluorination of the corresponding δ-chloroimines using NFSI (N-fluorodibenzenesulfonimide) in acetonitrile. After hydride reduction imino bond subsequent intramolecular substitution chloride atom, were obtained good yields. In addition, this methodology was applied to establish first N-protected 3,3-difluoropipecolic acid, fluorinated amino acid.
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