Enantioselective synthesis and chiroptical properties of optically active isoflavone epoxides

Albert Lévai, Waldemar Adam, Rainer T. Fell, Ralph Gessner, Tamás Patonay, András Simon, Gábor Tóth

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28 Citations (Scopus)

Abstract

Enantioselective epoxidation of isoflavones 1a-f has been performed by using Mn(III)salen complexes (R,R)-3 and (S,S)-3 as catalysts and dimethyldioxirane (DMD) or NaOCl together with 4-phenylpyridine N-oxide (PPNO) axial ligand as oxygen donors to obtain nonracemic isoflavone epoxides 2a-f. With the help of circular dichroism (CD) spectra of three enantiomeric pairs, and Snatzke's inverse octant role, the absolute configurations of these optically active isoflavone epoxides have been determined.

Original languageEnglish
Pages (from-to)13105-13114
Number of pages10
JournalTetrahedron
Volume54
Issue number43
DOIs
Publication statusPublished - Oct 22 1998

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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