Efficient epoxidation of electron-deficient olefins with a cationic manganese complex

被引:223
作者
Murphy, A [1 ]
Dubois, G [1 ]
Stack, TDP [1 ]
机构
[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA
关键词
D O I
10.1021/ja029962r
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The complex [MnII(R,R-mcp)(CF3SO3)2] is an efficient and practical catalyst for the epoxidation of electron-deficient olefins. This catalyst is capable of epoxidizing olefins with as little as 0.1 mol % catalyst in under 5 min using 1.2 equiv of peracetic acid as the terminal oxidant. A wide scope of substrates are epoxidized including terminal, tertiary, cis and trans internal, enones, and methacrylates with >85% isolated yields. Copyright © 2003 American Chemical Society.
引用
收藏
页码:5250 / 5251
页数:2
相关论文
共 25 条
[1]   SYNTHESIS AND CHARACTERIZATION OF COMPLEXES CONTAINING THE (MU-OXO)(MU-ACETATO)DIMANGANESE(III/III) CORE [J].
ARULSAMY, N ;
GLERUP, J ;
HAZELL, A ;
HODGSON, DJ ;
MCKENZIE, CJ ;
TOFTLUND, H .
INORGANIC CHEMISTRY, 1994, 33 (14) :3023-3025
[2]   PORPHYRINS AND AZAPORPHINES AS CATALYSTS IN ALKENE EPOXIDATIONS WITH PERACETIC-ACID [J].
BANFI, S ;
MONTANARI, F ;
QUICI, S ;
BARKANOVA, SV ;
KALIYA, OL ;
KOPRANENKOV, VN ;
LUKYANETS, EA .
TETRAHEDRON LETTERS, 1995, 36 (13) :2317-2320
[3]   MONOOXYGENASE-LIKE OXIDATION OF HYDROCARBONS BY H2O2 CATALYZED BY MANGANESE PORPHYRINS AND IMIDAZOLE - SELECTION OF THE BEST CATALYTIC-SYSTEM AND NATURE OF THE ACTIVE OXYGEN SPECIES [J].
BATTIONI, P ;
RENAUD, JP ;
BARTOLI, JF ;
REINAARTILES, M ;
FORT, M ;
MANSUY, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (25) :8462-8470
[4]  
CHE CM, 1991, J CHEM RES-S, P30
[5]   An efficient catalyst for asymmetric epoxidation of terminal olefins [J].
Collman, JP ;
Wang, Z ;
Straumanis, A ;
Quelquejeu, M ;
Rose, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (02) :460-461
[6]   A simple and efficient method for epoxidation of terminal alkenes [J].
Coperet, C ;
Adolfsson, H ;
Sharpless, KB .
CHEMICAL COMMUNICATIONS, 1997, (16) :1565-1566
[7]   Modeling Rieske dioxygenases:: The first example of iron-catalyzed asymmetric cis-dihydroxylation of olefins [J].
Costas, M ;
Tipton, AK ;
Chen, K ;
Jo, DH ;
Que, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (27) :6722-6723
[8]   Epoxidation of terminal or electron-deficient olefins with H2O2, catalysed by Mn-trimethyltriazacyclonane complexes in the presence of an oxalate buffer [J].
De Vos, DE ;
Sels, BF ;
Reynaers, M ;
Rao, YVS ;
Jacobs, PA .
TETRAHEDRON LETTERS, 1998, 39 (20) :3221-3224
[9]   Highly selective epoxidation of alkenes and styrenes with H2O2 and manganese complexes of the cyclic triamine 1,4,7-trimethyl-1,4,7-triazacyclononane [J].
DeVos, D ;
Bein, T .
CHEMICAL COMMUNICATIONS, 1996, (08) :917-918
[10]   THE DETERMINATION OF THE PARAMAGNETIC SUSCEPTIBILITY OF SUBSTANCES IN SOLUTION BY NUCLEAR MAGNETIC RESONANCE [J].
EVANS, DF .
JOURNAL OF THE CHEMICAL SOCIETY, 1959, (JUN) :2003-2005