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

F. Fülöp, Ferenc Miklós, E. Forró

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

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Cyclopentanes
Pyrimidines
Carboxylic Acids
Microwaves
Derivatives
Acids
levulinic acid
pyrrolopyrimidine

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Diexo-3-aminonorbornane-2-carboxylic acid as highly applicable chiral, source for the enantioselective synthesis of heterocycles. / Fülöp, F.; Miklós, Ferenc; Forró, E.

In: Synlett, No. 11, 01.07.2008, p. 1687-1689.

Research output: Contribution to journalArticle

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AB - 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.

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