Biomimetic Iron-Catalyzed Asymmetric Epoxidations: Fundamental Concepts, Challenges and Opportunities

被引:60
作者
Gelalcha, Feyissa Gadissa [1 ]
机构
[1] Texas A&M Univ Kingsville, Dept Chem, Kingsville, TX 78363 USA
关键词
asymmetric catalysis; epoxides; green chemistry; iron; oxidation; SOLUBLE METHANE MONOOXYGENASE; O BOND-CLEAVAGE; OLEFIN CIS-DIHYDROXYLATION; AQUEOUS HYDROGEN-PEROXIDE; HIGH-VALENT IRON; COUPLED ELECTRON-TRANSFER; ISOPENICILLIN N-SYNTHASE; C-H HYDROXYLATION; NONHEME IRON; ENANTIOSELECTIVE EPOXIDATION;
D O I
10.1002/adsc.201300716
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The state-of-the-art in the non-enzymatic iron-catalyzed asymmetric epoxidation of CC double bonds is reviewed within the broader context of biomimetic oxidation catalysis. After introducing fundamental concepts of oxygen activation in nature and by man, historical landmarks, recent breakthroughs, scopes and limitations in relation to existing methodologies and their impact on future directions are assessed, focusing mainly on progress made in the last five years.
引用
收藏
页码:261 / 299
页数:39
相关论文
共 278 条
[61]   Spectroscopy and electronic structures of mono- and binuclear high-valent non-heme iron-oxo systems [J].
Decker, Andrea ;
Clay, Michael D. ;
Solomon, Edward I. .
JOURNAL OF INORGANIC BIOCHEMISTRY, 2006, 100 (04) :697-706
[62]  
DEMONTELLANO PRO, 1984, MOL PHARMACOL, V25, P310
[63]   Molecular chemistry of consequence to renewable energy [J].
Dempsey, JL ;
Esswein, AJ ;
Manke, DR ;
Rosenthal, J ;
Soper, JD ;
Nocera, DG .
INORGANIC CHEMISTRY, 2005, 44 (20) :6879-6892
[64]   Formation and decay of hydroperoxo-ferric heme complex in horseradish peroxidase studied by cryoradiolysis [J].
Denisov, IG ;
Makris, TM ;
Sligar, SG .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2002, 277 (45) :42706-42710
[65]   Cryotrapped reaction intermediates of cytochrome P450 studied by radiolytic reduction with phosphorus-32 [J].
Denisov, IG ;
Makris, TM ;
Sligar, SG .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2001, 276 (15) :11648-11652
[66]   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
[67]   The active intermediates of non-heme-iron-based systems for catalytic alkene epoxidation with H2O2/CH3COOH [J].
Duban, Eduard A. ;
Bryliakov, Konstantin P. ;
Talsi, Evgenii P. .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2007, (06) :852-857
[68]   Simple iron catalyst for terminal alkene epoxidation [J].
Dubois, G ;
Murphy, A ;
Stack, TDP .
ORGANIC LETTERS, 2003, 5 (14) :2469-2472
[69]   Measurement of Intrinsic Rate Constants in the Tyrosine Hydroxylase Reaction [J].
Eser, Bekir E. ;
Fitzpatrick, Paul F. .
BIOCHEMISTRY, 2010, 49 (03) :645-652
[70]   Catalytic asymmetric oxidation of sulfide and styrene derivatives using macroporous resins containing chiral metalloporphyrins (Fe, Ru) [J].
Ferrand, Yann ;
Daviaud, Romain ;
Le Maux, Paul ;
Simonneaux, Grard .
TETRAHEDRON-ASYMMETRY, 2006, 17 (06) :952-960