6533b82afe1ef96bd128b969
RESEARCH PRODUCT
Syntheses of Four Enantiomers of 2,3-Diendo- and 3-Endo-aminobicyclo[2.2.2]oct-5-ene-2-exo-carboxylic Acid and Their Saturated Analogues
Márta PalkóFerenc FülöpReijo SillanpääMikko M. Hänninensubject
StereochemistryCarboxylic acidCarboxylic AcidsPharmaceutical ScienceArticleAnalytical Chemistrylcsh:QD241-441Hydrolysislcsh:Organic chemistryDrug DiscoveryMoleculePhysical and Theoretical Chemistryta116Nuclear Magnetic Resonance BiomolecularEne reactionchemistry.chemical_classificationMolecular StructureChemistryOrganic ChemistryDiastereomerresolutionconstrained chiral β-amino acidsEstersNuclear magnetic resonance spectroscopycontinuous flow hydrogenationsChemistry (miscellaneous)bicyclic β-amino acid derivativesMolecular MedicineEnantiomercontinuous flow hydrogenations<b> </b>bicyclic beta-amino acid derivativesIsomerizationconstrained chiral beta-amino acidsdescription
Abstract: Ethyl 2,3- diendo -3-aminobicyclo[2.2.2]oct- 5-ene-2-carboxylate ((±)- 1 ) was resolved with O , O '-dibenzoyltartaric acid via diastere omeric salt formation. The efficient synthesis of the enantiomers of 2,3- diendo -3-aminobicyclo[2.2.2]oct- 5-ene-2-carboxylic acid ((+)- 7 and (–)- 7 ), 3- endo -aminobicyclo[2.2.2]oct-5-ene-2- exo -carboxylic acid ((+)- 5 and (–)- 5 ), cis - and trans -3-aminobicyclo[2.2.2]octa ne-2-carboxylic acid ((+)- 6 , (–)- 6 , (+)- 8 and (–)- 8 ) was achieved via isomerization, hydrogenation and hydrolysis of the corresponding esters (–)- 1 and (+)- 1 . The stereochemistry and relative configurations of the synthesized compounds were determined by NMR spectroscopy (based on the 3 J (H,H) coupling constants) and X-ray crystallography. peerReviewed
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2013-12-01 |