6533b827fe1ef96bd128669f

RESEARCH PRODUCT

Regio- and diastereoselective fluorination of alicyclic β-amino acids.

Loránd KissFerenc FülöpFerenc FülöpSantos FusteroEnikő Forró

subject

chemistry.chemical_classificationModels MolecularCyclohexaneBicyclic moleculeStereochemistryOrganic ChemistryIodolactonizationMolecular ConformationStereoisomerismCrystallography X-RayBiochemistryAmino acidchemistry.chemical_compoundAlicyclic compoundchemistryOrganic chemistryStereoselectivityPhysical and Theoretical ChemistryEnantiomerAmino AcidsLactone

description

A regio- and stereoselective approach to fluorinated β-aminocyclohexene or cyclohexane esters has been developed, starting from a bicyclic β-lactam (1). The procedure involves six or seven steps, based on regio- and stereoselective iodolactonization, lactone opening and hydroxy–fluorine exchange. The method has been extended to the synthesis of fluorinated amino ester enantiomers.

10.1039/c1ob05648dhttps://pubmed.ncbi.nlm.nih.gov/21773624