Asymmetric organocatalysis: An efficient enantioselective access to benzopyranes and chromenes

Magnus Rueping*, Erli Sugiono, Estíbaliz Merino

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

173 Scopus citations

Abstract

A method was proposed for the development of diaryl prolinol by catalyzed and enatioselective reaction of diketones with α,β-unsaturated aldehydes to produce biologically active chromenones. The study found that the reaction of α-β-unsaturated aldehydes with a chiral secondary amine can produce an intermediary iminium ion. The study observed that catalysis of the transformation can be achieved and the chromenone can be isolated in good yields. The study also observed that the enantioselective addition-cyclization cascade reaction of diketone with aldehyde and 10 mol% of dyarylprolinol catalyst can produce the 2-hydroxychromenone in a yield of 78%. The organocatalytic addition-acetalization reaction can be used to produce 2-hydroxychromenones with different aliphatic and aromatic substituents.

Original languageEnglish (US)
Pages (from-to)6329-6332
Number of pages4
JournalChemistry - A European Journal
Volume14
Issue number21
DOIs
StatePublished - Jul 18 2008

Keywords

  • Asymmetric catalysis
  • Brønsted acids
  • Chromenes
  • Domino reactions
  • Organocatalysis

ASJC Scopus subject areas

  • Chemistry(all)

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