Molecules 2013, 18(12), 15080-15093; doi:10.3390/molecules181215080
Article

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

1email, 2email, 2email and 1,3,* email
Received: 11 November 2013; in revised form: 2 December 2013 / Accepted: 3 December 2013 / Published: 6 December 2013
(This article belongs to the Section Organic Synthesis)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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.
Keywords: bicyclic β-amino acid derivatives; constrained chiral β-amino acids; resolution; continuous flow hydrogenations
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MDPI and ACS Style

Palkó, M.; Hänninen, M.M.; Sillanpää, R.; Fülöp, F. 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 2013, 18, 15080-15093.

AMA Style

Palkó M, Hänninen MM, Sillanpää R, Fülöp F. 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. 2013; 18(12):15080-15093.

Chicago/Turabian Style

Palkó, Márta; Hänninen, Mikko M.; Sillanpää, Reijo; Fülöp, Ferenc. 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, no. 12: 15080-15093.


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