Ring closure reactions of bicyclic prolinol and prolin ester enantiomers

Márta Palkó, Zsuzsa Molnár, Henri Kivelä, Jari Sinkkonen, Kalevi Pihlaja, Ferenc Fülöp

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Starting from the of bicyclic proline ester, ethyl exo-2-azabicyclo[2.2.1] heptane-3-carboxylate (+)-5 several hydantoines and thiohydantoines were prepared by acidic ring closure of the corresponding urea or thiourea derivatives. Enantiomer (-)-5 was reduced to 2-azanorbornylmethanol 12, which was transformed to 5,8-methanooxazolo- and thiazolo[3,4-a]pyridine derivatives. The structures, stereochemistry and relative configurations of the synthesized compounds were proved by NMR.

Original languageEnglish
Pages (from-to)221-234
Number of pages14
JournalArkivoc
Volume2009
Issue number6
DOIs
Publication statusPublished - Apr 8 2009

Keywords

  • 1,3-heterocycles
  • Bicyclic prolinol
  • Enantioselective synthesis
  • Epimerisation
  • Ring closure

ASJC Scopus subject areas

  • Organic Chemistry

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    Palkó, M., Molnár, Z., Kivelä, H., Sinkkonen, J., Pihlaja, K., & Fülöp, F. (2009). Ring closure reactions of bicyclic prolinol and prolin ester enantiomers. Arkivoc, 2009(6), 221-234. https://doi.org/10.3998/ark.5550190.0010.623