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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

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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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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