Asymmetric cyclization of 2′-hydroxychalcones to flavanones: Catalysis by chiral Brønsted acids and bases

Claudia Dittmer, Gerhard Raabe, Lukas Hintermann

Research output: Contribution to journalArticlepeer-review

80 Scopus citations

Abstract

The asymmetric cyclization of 2′-hydroxychalcones to flavanones is a basic, enzyme-catalyzed step in the biosynthesis of flavonoid natural products, but poses a long-standing problem for asymmetric catalysis with small molecule catalysts. Earlier claims concerning the realization of an asymmetric flavanone synthesis by means of camphorsulfonic acid as chiral Brønsted acid catalysts were reinvestigated using accurate HPLC methods for quantification of enantiomer ratios. The previous claims of asymmetric induction were thus shown to be untenable. On the other hand, cinchona alkaloids serve as chiral Brønsted base mediators for the asymmetric cyclization of either 6′-substituted 2′-hydroxychalcones or 2′,6′- dihydroxychalcones. 2′,6′-Dihydroxy-4,4′-dimethoxychalcone, for instance, cyclized to give the naturally occurring naringenin-4′,7- dimethyl ether in up to 64 % ee at 81 % conversion. The catalysis shows a marked dependency of the enantiomeric excess of the product on the catalyst, solvent and reactant concentration. Based on these successful examples of asymmetric cyclizations of 2′-hydroxychalcones to flavanones, requirements for more active asymmetric catalysts can be defined.

Original languageEnglish
Pages (from-to)5886-5898
Number of pages13
JournalEuropean Journal of Organic Chemistry
Issue number35
DOIs
StatePublished - 2007
Externally publishedYes

Keywords

  • Asymmetric catalysis
  • Chiral Brønsted acid
  • Cyclization
  • Flavanones
  • Oxygen heterocycles

Fingerprint

Dive into the research topics of 'Asymmetric cyclization of 2′-hydroxychalcones to flavanones: Catalysis by chiral Brønsted acids and bases'. Together they form a unique fingerprint.

Cite this