Enantioselective synthesis and chiroptical properties of optically active isoflavone epoxides

被引：31

作者：

Lévai, A

Adam, W

Fell, RT

Gessner, R

Patonay, T

Simon, A

Tóth, G

机构：

[1] Lajos Kossuth Univ, Dept Organ Chem, H-4010 Debrecen, Hungary

[2] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany

[3] Tech Univ Budapest, Hungarian Acad Sci, Inst Gen & Analyt Chem, Tech Analyt Res Grp, H-1111 Budapest, Hungary

来源：

TETRAHEDRON | 1998年 / 54卷 / 43期

关键词：

D O I：

10.1016/S0040-4020(98)00793-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 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 Snatzkes inverse octant rule, the absolute configurations of these optically active isoflavone epoxides have been determined, (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：13105 / 13114

页数：10

共 38 条

[1] ADAM W, 1992, SYNTHESIS-STUTTGART, P436
[2] Enantioselective epoxidation of isoflavones by Jacobsen's Mn(III)salen catalysts and dimethyldioxirane oxygen-atom source
Adam, W
Fell, RT
Lévai, A
Patonay, T
Peters, K
Simon, A
Tóth, G
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (07) : 1121 - 1124
[3] ADAM W, 1995, LIEBIGS ANN, P1547
[4] Synthesis of optically active α-hydroxy carbonyl compounds by the catalytic, enantioselective oxidation of silyl enol ethers and ketene acetals with (salen)manganese(III) complexes
Adam, W
Fell, RT
Stegmann, VR
Saha-Möller, CR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (04) : 708 - 714
[5] ENANTIOSELECTIVE EPOXIDATION OF 2,2-DIMETHYL-2H-CHROMENES BY DIMETHYLDIOXIRANE AND JACOBSENS MN(III)SALEN CATALYSTS
ADAM, W
JEKO, J
LEVAI, A
NEMES, C
PATONAY, T
SEBOK, P
[J]. TETRAHEDRON LETTERS, 1995, 36 (21) : 3669 - 3672
[6] A CONVENIENT PREPARATION OF ACETONE SOLUTIONS OF DIMETHYLDIOXIRANE
ADAM, W
BIALAS, J
HADJIARAPOGLOU, L
[J]. CHEMISCHE BERICHTE, 1991, 124 (10) : 2377 - 2377
[7] Determination of the absolute configuration of optically active 2,2-dimethyl-3,4-epoxychromans prepared by the catalytic enantioselective epoxidation with the dimethyldioxirane/Jacobsen Mn(III)salen system
Adam, W
Jeko, J
Levai, A
Majer, Z
Nemes, C
Patonay, T
Parkanyi, L
Sebok, P
[J]. TETRAHEDRON-ASYMMETRY, 1996, 7 (08) : 2437 - 2446
[8] ABSOLUTE-CONFIGURATION OF BENZOCYCLOBUTENE HOMOISOFLAVANONES FROM MUSCARI SPECIES
ADINOLFI, M
BARONE, G
GIORDANO, F
LANZETTA, R
PARRILLI, M
[J]. TETRAHEDRON, 1990, 46 (18) : 6565 - 6574
[9] ACID-CATALYZED COUPLING REACTIONS AND CONVERSIONS OF ISOFLAVONE EPOXIDES
BEZUIDENHOUDT, BCB
BRANDT, EV
FERREIRA, D
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (05): : 1081 - 1087
[10] ALPHA-HALOGENOKETONES .13. CHROMONE EPOXIDES - THEIR SYNTHESIS AND ACID-CATALYZED REARRANGEMENT
DONNELLY, JA
MALONEY, DE
[J]. TETRAHEDRON, 1979, 35 (24) : 2875 - 2881

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