6533b860fe1ef96bd12c386b

RESEARCH PRODUCT

Synthesis of fluorinated piperidine and azepane β-amino acid derivatives

Pablo BarrioLoránd KissFerenc FülöpFerenc FülöpRenata Anita Abrahami

subject

chemistry.chemical_classificationDouble bondBicyclic molecule010405 organic chemistryHydrochlorideStereochemistryOrganic Chemistry010402 general chemistryRing (chemistry)01 natural sciencesBiochemistryReductive amination0104 chemical sciencesAmino acidchemistry.chemical_compoundAzepanechemistryDrug DiscoveryPiperidine

description

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 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.

yearjournalcountryeditionlanguage
2016-11-01Tetrahedron
https://doi.org/10.1016/j.tet.2016.10.005