Highly Stereoselective Epoxidation with H2O2 Catalyzed by Electron-Rich Aminopyridine Manganese Catalysts

被引：78
作者：
Cusso, Olaf
Garcia-Bosch, Isaac
Font, David
Ribes, Xavi
Lloret-Fillol, Julio
Costas, Miquel [1 ]
机构：
[1] Univ Girona, IQCC, Campus Montilivi, E-17071 Girona, Catalonia, Spain
来源：
ORGANIC LETTERS | 2013年 / 15卷 / 24期
关键词：
ASYMMETRIC EPOXIDATION; ENANTIOSELECTIVE EPOXIDATION; UNSATURATED STEROIDS; IRON COMPLEXES; ALKENES; OXIDATION; EFFICIENT; OLEFINS; ACID;
D O I：
10.1021/ol403018x
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Fast, efficient, and highly stereoselective epoxidation with H2O2 is reached by manganese coordination complexes with e-rich aminopyridine tetradentate ligands. It is shown that the electronic properties of these catalysts vary systematically with the stereoselectivity of the O-atom transfer event and exert fine control over the activation of hydrogen peroxide, reducing the amount of carboxylic acid co-catalyst necessary for efficient operation.
引用
收藏
页码：6158 / 6161
页数：4
相关论文
共 33 条
[1]   A Study of the Epoxidation of Cycloolefins by the t-BuOH Copper-Permanganate System [J].
Baqi, Younis ;
Giroux, Simon ;
Corey, E. J. .
ORGANIC LETTERS, 2009, 11 (04) :959-961
[2]   Mn-trimethyltriazacyclononane/ascorbic acid: a remarkably efficient catalyst for the epoxidation of olefins and the oxidation of alcohols with hydrogen peroxide [J].
Berkessel, A ;
Sklorz, CA .
TETRAHEDRON LETTERS, 1999, 40 (45) :7965-7968
[3]   Catalytic Epoxidation of Alkenes by the Manganese Complex of a Reduced Porphyrinogen Macrocycle [J].
Bruyneel, Frederic ;
Letondor, Christophe ;
Bastuerk, Bjorn ;
Gualandi, Andrea ;
Pordea, Anca ;
Stoeckli-Evans, Helen ;
Neier, Reinhard .
ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (2-3) :428-440
[4]   Asymmetric epoxidation of unsaturated hydrocarbons catalyzed by ruthenium complexes [J].
Chatterjee, Debabrata .
COORDINATION CHEMISTRY REVIEWS, 2008, 252 (1-2) :176-198
[5]   Asymmetric Epoxidation with H2O2 by Manipulating the Electronic Properties of Non-heme Iron Catalysts [J].
Cusso, Olaf ;
Garcia-Bosch, Isaac ;
Ribas, Xavi ;
Lloret-Fillol, Julio ;
Costas, Miquel .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (39) :14871-14878
[6]   Asymmetric Epoxidation of Alkenes Catalyzed by a Porphyrin-Inspired Manganese Complex [J].
Dai, Wen ;
Li, Jun ;
Li, Guosong ;
Yang, Hua ;
Wang, Lianyue ;
Gao, Shuang .
ORGANIC LETTERS, 2013, 15 (16) :4138-4141
[7]   Asymmetric catalysis using iron complexes - 'Ruthenium Lite'? [J].
Darwish, Muftah ;
Wills, Martin .
CATALYSIS SCIENCE & TECHNOLOGY, 2012, 2 (02) :243-255
[8]   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
[9]   Recent advances in catalytic asymmetric epoxidation using the environmentally benign oxidant hydrogen peroxide and its derivatives [J].
De Faveri, Giorgio ;
Ilyashenko, Gennadiy ;
Watkinson, Michael .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (03) :1722-1760
[10]   Asymmetric epoxidation of electron-deficient olefins [J].
Diez, David ;
Nunez, Marta G. ;
Anton, Ana B. ;
Garcia, P. ;
Moro, R. F. ;
Garrido, N. M. ;
Marcos, Isidro S. ;
Basabe, P. ;
Urones, Julio G. .
CURRENT ORGANIC SYNTHESIS, 2008, 5 (03) :186-216
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