Diexo-3-aminonorbornane-2-carboxylic acid as highly applicable chiral, source for the enantioselective synthesis of heterocycles

Ferenc Fülöp, Ferenc Miklós, Eniko Forróa

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Diastereomers of tetracyclic pyrrolopyrimidine derivatives 2 and 3 were prepared in a three-step domino reaction from diexo-3-aminobicyclo[2.2.1]hept-5- ene-2-carboxamide with levulinic acid or p-toluoylpropionic acid. When subjected to a microwave-mediated retro-Diels-Alder reaction, these tetracycles furnished bicyclic pyrrolo[1,2-a]pyrimidines through the loss of cyclopentadiene. When enantiomeric diexo-3-aminobicyclo 2.2.1]hept-5-ene-2-carboxamide was used, the products were enantiomeric heterocycles with ee >99%, demonstrating that the title compound is an excellent chiral source.

Original languageEnglish
Pages (from-to)1687-1689
Number of pages3
JournalSynlett
Issue number11
DOIs
Publication statusPublished - Jul 1 2008

Keywords

  • Asymmetric synthesis
  • Chiral source
  • Chirality transfer
  • Domino reactions
  • Retro reactions
  • Ring closure
  • β-amino acids

ASJC Scopus subject areas

  • Organic Chemistry

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