Asymmetric Brønsted acid catalysis: Catalytic enantioselective synthesis of highly biologically active dihydroquinazolinones

Magnus Rueping*, Andrey P. Antonchick, Erli Sugiono, Konstantin Grenader

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

175 Scopus citations

Abstract

(Chemical Equation Presented) Surprisingly straightforward: A metal-free, highly enantioselective Brønsted acid catalyzed condensation/addition reaction has been developed for the construction of 2,3-dihydroquinazolinones starting from 2-aminobenzamide and aldehydes (see scheme). This efficient approach provides 2,3-dihydroquinazolinones with a strong preference for the S enantiomers, which have higher biological activities than the R enantiomers.

Original languageEnglish (US)
Pages (from-to)908-910
Number of pages3
JournalAngewandte Chemie - International Edition
Volume48
Issue number5
DOIs
StatePublished - Jan 19 2009

Keywords

  • Antitumor agents
  • Inhibitors
  • Organocatalysis
  • Phosphoric acid diester

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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