Synthesis of fluorinated piperidine and azepane β-amino acid derivatives

Renáta Anita Ábrahámi, L. Kiss, Pablo Barrio, Ferenc Fülöp

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11 Citations (Scopus)

Abstract

A convenient and robust stereocontrolled procedure has been developed for the synthesis of novel trifluoromethyl-containing piperidine and azepane β-amino ester stereoisomers. The synthesis started from readily available unsaturated bicyclic β-lactams and was based on oxidative cleavage of the ring C[dbnd]C double bond followed by ring closure of the diformyl intermediates in the presence of 2,2,2-trifluoroethylamine hydrochloride through reductive amination. The synthetic procedure has efficiently been extended towards the synthesis of mono- and difluorinated analogs.

Original languageEnglish
Pages (from-to)7526-7535
Number of pages10
JournalTetrahedron
Volume72
Issue number47
DOIs
Publication statusPublished - Nov 24 2016

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Keywords

  • Amino acid
  • Azaheterocycle
  • Fluorine
  • Reductive amination
  • Ring closing
  • Stereocontrol

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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