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
Palkó, M., Hänninen, M., Sillanpää, R., & Fülöp, F. (2013). 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. Molecules, 18 (12), 15080-15093. doi:10.3390/molecules181215080 Retrieved from http://www.mdpi.com/1420-3049/18/12/15080
DisciplineEpäorgaaninen ja analyyttinen kemia
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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.
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