Asymmetric iminium ion catalysis: An efficient enantioselective synthesis of pyranonaphthoquinones and β-lapachones

Magnus Rueping*, Erli Sugiono, Estíbaliz Merino

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

137 Scopus citations

Abstract

(Chemical Equation Presented) An addition-cyclization reaction cascade triggeredby an organocatalyst was used for the enantioselective preparation of a series of biologically active 1,2- and 1,4-pyranonaphthoquinones from aliphatic andaromatic α,β-unsaturated aldehydes and2-hydroxy-1-4- naphthoquinone. A trimethylsilyl-protected diarylprolinol serves as the Lewis base organocatalyst.

Original languageEnglish (US)
Pages (from-to)3046-3049
Number of pages4
JournalAngewandte Chemie - International Edition
Volume47
Issue number16
DOIs
StatePublished - Apr 7 2008

Keywords

  • Iminium ions
  • Lapachones
  • Lewis base catalysis
  • Naphthoquinones
  • Organocatalysis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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