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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

1
,
2
,
2
 and
1,3,*
1 Institute of Pharmaceutical Chemistry, University of Szeged, Szeged H-6720, Eötvös utca 6, Hungary 2 Department of Chemistry, University of Jyväskylä, Turku FIN-40014, Finland 3 Stereochemistry Research Group of the Hungarian Academy of Sciences, University of Szeged, Szeged H-6720, Eötvös utca 6, Hungary
* Author to whom correspondence should be addressed.
Received: 11 November 2013 / Revised: 2 December 2013 / Accepted: 3 December 2013 / Published: 6 December 2013
(This article belongs to the Section Organic Synthesis)
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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 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 bicyclic β-amino acid derivatives; constrained chiral β-amino acids; resolution; continuous flow hydrogenations
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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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.

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