Retro-Diels-Alder protocol for the synthesis of pyrrolo[1,2-a]pyrimidine and pyrimido[2,1-a]isoindole enantiomers

Ferenc Miklós, Zita Tóth, Mikko M. Hänninen, Reijo Sillanpää, Eniko Forró, Ferenc Fülöp

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

A simple protocol was introduced to prepare several enantiomerically pure heterocycles by using (-)-(1R,2R,3S,4S)-3-aminonorbornene-2-carboxylic acid as a chiral auxiliary. The protocol is based on a domino ring-closure reaction, in which the relative configuration of the new asymmetric center is controlled by the stereochemistry of the amino acid, followed by a microwave-induced retro-Diels-Alder reaction.

Original languageEnglish
Pages (from-to)4887-4894
Number of pages8
JournalEuropean Journal of Organic Chemistry
Issue number22
DOIs
Publication statusPublished - Aug 1 2013

Keywords

  • Chiral auxiliaries
  • Domino reactions
  • Microwave chemistry
  • Nitrogen heterocycles
  • Synthetic methods

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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