ENANTIOSELECTIVE SYNTHESIS AND CHIROPTICAL PROPERTIES OF OPTICALLY-ACTIVE ISOFLAVONE EPOXIDES

Authors
LEVAI A ADAM W FELL RT GESSNER R PATONAY T SIMON A TOTH G
Citation
A. Levai et al., ENANTIOSELECTIVE SYNTHESIS AND CHIROPTICAL PROPERTIES OF OPTICALLY-ACTIVE ISOFLAVONE EPOXIDES, Tetrahedron, 54(43), 1998, pp. 13105-13114
Citations number
38
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
43
Year of publication
1998
Pages
13105 - 13114
Database
ISI
SICI code
0040-4020(1998)54:43<13105:ESACPO>2.0.ZU;2-7
Abstract
Enantioselective epoxidation of isoflavones 1a-f has been performed by using Mn(III)salen complexes (I,R)-3 and (S,S)-3 as catalysts and dim ethyldioxirane (DMD) or NaOCl together with 4-phenylpyridine N-oxide ( PPNO) axial ligand as oxygen donors to obtain nonracemic isoflavone ep oxides 2a-f. With the help of circular dichroism (CD) spectra of three enantiomeric pairs, and Snatzkes inverse octant rule, the absolute co nfigurations of these optically active isoflavone epoxides have been d etermined, (C) 1998 Elsevier Science Ltd. All rights reserved.