Circular dichroism and absolute configuration of Aza‐ and Thiaflavanones

S. Antus, E. Gács-Baitz, Judit Kajtár, Günther Snatzke, Adrienne L. Tőkés

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

The correlation between the absolute configuration and CD of aza‐ and thiaflavanone (1, 2) is discussed: the 2R configuration for the laevorotatory enantiomers has been established by a comparison of their CD data with those of (S)‐(−)‐3. For the Cotton effect within the n → π* band of 1 and 2 the same helicity rule is valid as for the homochirally analogous flavanones (3). Starting from (S)‐(−)‐flavanone (3) and cholesterol (5), we have synthesized the chromane derivatives 4 and 20, respectively. The 1Lb band of the chromane chromophore has been unequivocally identified in the range between 255 and 290 nm in the CD spectra of 4 and 20. For this Cotton effect the opposite helicity rule is valid as compared with the homochirally analogous tetralins: the P/M helicity of the hetero ring leads to a negative/positive CD within the 1Lb band. The modification of the helicity rule can be explained with the help of Petruska's “q values”. (Formula Presented.)

Original languageEnglish
Pages (from-to)497-502
Number of pages6
JournalLiebigs Annalen der Chemie
Volume1994
Issue number5
DOIs
Publication statusPublished - 1994

Keywords

  • Azaflavanones
  • Circular dichroism
  • Steroids
  • Thiaflavanones

ASJC Scopus subject areas

  • Medicine(all)

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