Practical manganese-catalysed highly enantioselective cis-dihydroxylation of electron-deficient alkenes and detection of a cis-dioxomanganese(V) intermediate by high resolution ESI-MS analysis

被引：58
作者：
Chow, Toby Wai-Shan
Liu, Yungen
Che, Chi-Ming [1 ]
机构：
[1] Univ Hong Kong, Dept Chem, State Key Lab Synthet Chem, Hong Kong, Hong Kong, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2011年 / 47卷 / 40期
关键词：
COMPLEX; OLEFINS; EPOXIDATION; H2O2; OXIDATIONS; PORPHYRINS; REACTIVITY; MECHANISM; LIGAND; OXO;
D O I：
10.1039/c1cc11999k
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A practical protocol has been developed for asymmetric cis-dihydroxylation of electron-deficient alkenes with Oxone catalysed by a manganese complex bearing a chiral tetradentate N(4)-donor ligand affording cis-diols in up to 95% yield with up to 96% ee. Analysis of the reaction mixture by high resolution ESI-MS revealed the formation of a cis-dioxomanganese(V) intermediate.
引用
收藏
页码：11204 / 11206
页数：3
相关论文
共 22 条
[1]   HIGHLY ENANTIOSELECTIVE, CATALYTIC EPOXIDATION OF TRISUBSTITUTED OLEFINS [J].
BRANDES, BD ;
JACOBSEN, EN .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (16) :4378-4380
[2]   cis-Dihydroxylation of Alkenes with Oxone Catalyzed by Iron Complexes of a Macrocyclic Tetraaza Ligand and Reaction Mechanism by ESI-MS Spectrometry and DFT Calculations [J].
Chow, Toby Wai-Shan ;
Wong, Ella Lai-Ming ;
Guo, Zhen ;
Liu, Yungen ;
Huang, Jie-Sheng ;
Che, Chi-Ming .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (38) :13229-13239
[3]   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
[4]   Manganese catalysed asymmetric cis-dihydroxylation with H2O2 [J].
de Boer, Johannes W. ;
Browne, Wesley R. ;
Harutyunyan, Syuzanna R. ;
Bini, Laura ;
Tiemersma-Wegman, Theodora D. ;
Alsters, Paul L. ;
Hage, Ronald ;
Feringa, Ben L. .
CHEMICAL COMMUNICATIONS, 2008, (32) :3747-3749
[5]   Mechanism of cis-dihydroxylation and epoxidation of alkenes by highly H2O2 efficient dinuclear manganese catalysts [J].
de Boer, Johannes W. ;
Browne, Wesley R. ;
Brinksma, Jelle ;
Alsters, Paul L. ;
Hage, Ronald ;
Feringa, Ben L. .
INORGANIC CHEMISTRY, 2007, 46 (16) :6353-6372
[6]  
Eliel E.L., 2001, BASIC ORGANIC STEREO
[7]   Ligand topology variations and the importance of ligand field strength in non-heme iron catalyzed oxidations of alkanes [J].
England, Jason ;
Britovsek, George J. P. ;
Rabadia, Nitin ;
White, Andrew J. P. .
INORGANIC CHEMISTRY, 2007, 46 (09) :3752-3767
[8]   Why are olefins oxidized by RuO4 under cleavage of the carbon-carbon bond whereas oxidation by OsO4 yields cis-diols? [J].
Frunzke, J ;
Loschen, C ;
Frenking, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (11) :3642-3652
[9]   A mechanistic study of the epoxidation of cinnamic acid by hydrogen peroxide catalysed by manganese 1,4,7-trimethyl-1,4,7-triazacyclononane complexes [J].
Gilbert, BC ;
Smith, JRL ;
Payeras, AMI ;
Oakes, J ;
Prats, RPI .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2004, 219 (02) :265-272
[10]   Formation and reaction of O=MnV species in the oxidation of phenolic substrates with H2O2 catalysed by the dinuclear manganese(IV) 1,4,7-trimethyl-1,4,7-triazacyclononane complex [MnIV2(μ-O)3(TMTACN)2](PF6)2 [J].
Gilbert, BC ;
Smith, JRL ;
Payeras, AMI ;
Oakes, J .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (08) :1176-1180
123