Enantioselective epoxidation of isoflavones by Jacobsen's Mn(III)salen catalysts and dimethyldioxirane oxygen-atom source

被引:29
作者
Adam, W
Fell, RT
Lévai, A
Patonay, T
Peters, K
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] Max Planck Inst Festkorperforsch, D-70506 Stuttgart, Germany
[4] Tech Univ Budapest, Inst Gen & Analyt Chem, Hungarian Acad Sci, Tech Analyt Res Grp, H-1111 Budapest, Hungary
基金
匈牙利科学研究基金会;
关键词
D O I
10.1016/S0957-4166(98)00102-5
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The catalytic enantioselective epoxidation of the isoflavones 1a-f has been performed by the Mn(III)salen complexes (R,R)-3 and (S,S)-3 as catalysts and dimethyldioxirane as the oxygen-atom source to afford optically active isoflavone epoxides 2a-f, The absolute configuration of the nonracemic epoxides 2 have been determined by X-ray diffraction analysis. Our present results constitute the first examples of the preparation of optically active isoflavone epoxides. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1121 / 1124
页数:4
相关论文
共 25 条
[1]  
ADAM W, 1992, SYNTHESIS-STUTTGART, P436
[2]  
ADAM W, 1995, LIEBIGS ANN, P1547
[3]  
Adam W, 1996, B SOC CHIM BELG, V105, P581
[4]   ENANTIOSELECTIVE EPOXIDATION OF 2,2-DIMETHYL-2H-CHROMENES BY DIMETHYLDIOXIRANE AND JACOBSENS MN(III)SALEN CATALYSTS [J].
ADAM, W ;
JEKO, J ;
LEVAI, A ;
NEMES, C ;
PATONAY, T ;
SEBOK, P .
TETRAHEDRON LETTERS, 1995, 36 (21) :3669-3672
[5]   DIOXIRANES - A NEW CLASS OF POWERFUL OXIDANTS [J].
ADAM, W ;
CURCI, R ;
EDWARDS, JO .
ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (06) :205-211
[6]  
ADAM W, 1993, TOP CURR CHEM, V164, P45
[7]   A CONVENIENT PREPARATION OF ACETONE SOLUTIONS OF DIMETHYLDIOXIRANE [J].
ADAM, W ;
BIALAS, J ;
HADJIARAPOGLOU, L .
CHEMISCHE BERICHTE, 1991, 124 (10) :2377-2377
[8]   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 [J].
Adam, W ;
Jeko, J ;
Levai, A ;
Majer, Z ;
Nemes, C ;
Patonay, T ;
Parkanyi, L ;
Sebok, P .
TETRAHEDRON-ASYMMETRY, 1996, 7 (08) :2437-2446
[9]  
[Anonymous], ORGANIC PEROXIDES
[10]   ACID-CATALYZED COUPLING REACTIONS AND CONVERSIONS OF ISOFLAVONE EPOXIDES [J].
BEZUIDENHOUDT, BCB ;
BRANDT, EV ;
FERREIRA, D .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (05) :1081-1087