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

Márta Palkó, Mikko M. Hanninen, Reijo Sillanpaa, Ferenc Fulop

Research output: Contribution to journalArticle

4 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)15080-15093
Number of pages14
JournalMolecules
Volume18
Issue number12
DOIs
Publication statusPublished - Dec 2013

Keywords

  • Bicyclic β-amino acid derivatives
  • Constrained chiral β-amino acids
  • Continuous flow hydrogenations
  • Resolution

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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