title: 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.
abstract: Ethyl 2,3-diendo-3-aminobicyclo[2.2.2]oct-5-ene-2-carboxylate ((±)-1) was resolved with O,O'-dibenzoyltartaric acid via diastereomeric 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]octane-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 3J(H,H) coupling constants) and X-ray crystallography.
authors: Institute of Pharmaceutical Chemistry, University of Szeged, Szeged H-6720, Eötvös utca 6, Hungary. fulop@pharm.u-szeged.hu.
authors: Márta
authors: M
authors: Palkó
authors: Mikko M
authors: MM
authors: Hänninen
authors: Reijo
authors: R
authors: Sillanpää
authors: Ferenc
authors: F
authors: Fülöp
mesh_terms: D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular
chemical_list: D002264:Carboxylic Acids; D004952:Esters