Catalytic Asymmetric Synthesis of Chromene Derivatives by Iminium Ion Catalysis

Magnus Rueping*, Estíbaliz Merino, Erli Sugiono

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

The diarylprolinol TMS ether catalyzed enantioselective addition-acetalization cascade reaction of 1,3-diketones with α,β-unsaturated aldehydes provides access to biologically active hydroxychromenone derivatives. These chromenones can be converted into the corresponding lactones, oxadecalinones, and benzopyranes in good yields without loss of enantiomeric excess. The usefulness of this newly developed methodology was demonstrated in the synthesis of the core structure of a Δ 9-tetrahydrocannabinol analog.

Original languageEnglish (US)
Pages (from-to)987-992
Number of pages6
JournalChemCatChem
Volume4
Issue number7
DOIs
StatePublished - Jul 2012
Externally publishedYes

Keywords

  • Biological activity
  • Chromates
  • Cyclization
  • Enantioselectivity
  • Homogeneous catalysis

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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