Enantioselective synthesis and chiroptical properties of optically active isoflavone epoxides

A. Lévai, Waldemar Adam, Rainer T. Fell, Ralph Gessner, T. Patonay, A. Simon, Gábor Tóth

Research output: Contribution to journalArticle

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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Isoflavones
Epoxy Compounds
Epoxidation
Circular Dichroism
Oxides
Oxygen
Ligands
Catalysts

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Enantioselective synthesis and chiroptical properties of optically active isoflavone epoxides. / Lévai, A.; Adam, Waldemar; Fell, Rainer T.; Gessner, Ralph; Patonay, T.; Simon, A.; Tóth, Gábor.

In: Tetrahedron, Vol. 54, No. 43, 22.10.1998, p. 13105-13114.

Research output: Contribution to journalArticle

Lévai, A. ; Adam, Waldemar ; Fell, Rainer T. ; Gessner, Ralph ; Patonay, T. ; Simon, A. ; Tóth, Gábor. / Enantioselective synthesis and chiroptical properties of optically active isoflavone epoxides. In: Tetrahedron. 1998 ; Vol. 54, No. 43. pp. 13105-13114.
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