6533b7d7fe1ef96bd1268f13

RESEARCH PRODUCT

Efficient regio- and stereoselective access to novel fluorinated ?-aminocyclohexanecarboxylates

Loránd KissSantos FusteroMelinda NonnFerenc FülöpReijo Sillanpää

subject

stereoselective reactionDouble bondStereochemistrychemistry.chemical_elementaminohapotRing (chemistry)Full Research PaperhydroxylationHydroxylationlcsh:QD241-441chemistry.chemical_compoundlcsh:Organic chemistryepoxidationlcsh:Scienceta116chemistry.chemical_classificationamino acidsOrganic ChemistryfluorinationAmino acidChemistrychemistryFluorineStereoselectivitylcsh:Q

description

A regio- and stereoselective method has been developed for the synthesis of novel fluorinated 2-aminocyclohexanecarboxylic acid derivatives with the fluorine attached to position 4 of the ring. The synthesis starts from either cis- or trans-β-aminocyclohex-4-enecarboxylic acids and involves regio- and stereoselective transformation of the ring C–C double bond through iodooxazine formation and hydroxylation, followed by hydroxy–fluorine or oxo–fluorine exchange.

10.3762/bjoc.9.130http://juuli.fi/Record/0037177513