Synergistic Interplay of a Non-Heme Iron Catalyst and Amino Acid Coligands in H2O2 Activation for Asymmetric Epoxidation of α-Ayl-Substituted Styrenes

被引：72

作者：

Cusso, Olaf ^{[1
,2
]}

Ribas, Xavi ^{[1
,2
]}

Lloret-Fillol, Julio ^{[1
,2
]}

Costas, Miquel ^{[1
,2
]}

机构：

[1] Univ Girona, IQCC, Girona 17071, Catalonia, Spain

[2] Univ Girona, Dept Quim, Girona 17071, Catalonia, Spain

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 09期

基金：

欧洲研究理事会;

关键词：

amino acids; asymmetric catalysis; bioinspired catalysis; epoxidation; non-heme iron complexes; HIGHLY ENANTIOSELECTIVE EPOXIDATION; ALKENE EPOXIDATION; AROMATIC ALKENES; LIGANDS; OLEFINS; COMPLEXES; OXIDATION; DIHYDROXYLATION; HYDROGENATION; MECHANISMS;

D O I：

10.1002/anie.201410557

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Highly enantioselective epoxidation of -substituted styrenes with aqueous H2O2 is described by using a chiral iron complex as the catalyst and N-protected amino acids (AAs) as coligands. The amino acids synergistically cooperate with the iron center in promoting an efficient activation of H2O2 to catalyze epoxidation of this challenging class of substrates with good yields and stereoselectivities (up to 97%ee) in short reaction times.

引用

页码：2729 / 2733

页数：5

共 50 条

[21] Weak O2 binding and strong H2O2 binding at the non-heme diiron center of trypanosome alternative oxidase
Yamasaki, Sotaro
Shoji, Mitsuo
Kayanuma, Megumi
Sladek, Vladimir
Inaoka, Daniel Ken
Matsuo, Yuichi
Shiba, Tomoo
Young, Luke
Moore, Anthony L.
Kita, Kiyoshi
Shigeta, Yasuteru
BIOCHIMICA ET BIOPHYSICA ACTA-BIOENERGETICS, 2021, 1862 (04):
[22] Chemo- and stereoselective C-H oxidations and epoxidations/cis-dihydroxylations with H2O2, catalyzed by non-heme iron and manganese complexes
Talsi, Evgenii P.
Bryliakov, Konstantin P.
COORDINATION CHEMISTRY REVIEWS, 2012, 256 (13-14) : 1418 - 1434
[23] The active intermediates of non-heme-iron-based systems for catalytic alkene epoxidation with H2O2/CH3COOH
Duban, Eduard A.
Bryliakov, Konstantin P.
Talsi, Evgenii P.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2007, (06) : 852 - 857
[24] Non-heme iron polyazadentate complexes as catalysts for aromatic hydroxylation by H2O2:: Particular efficiency of tetrakis(2-pyridylmethyl)ethylenediamine-iron(II) complexes
Thibon, Aurore
Bartoli, Jean-Francois
Guillot, Regis
Sainton, Joelle
Martinho, Marlene
Mansuy, Daniel
Banse, Frederic
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2008, 287 (1-2) : 115 - 120
[25] Asymmetric Epoxidation of Olefins with H2O2 Catalyzed by a Bioinspired Aminopyridine N4 Iron Complex
Wang, Wenfang
Sun, Qiangsheng
Xu, Daqian
Xia, Chungu
Sun, Wei
CHEMCATCHEM, 2017, 9 (03) : 420 - 424
[26] Epoxidation of olefins with H2O2 catalyzed by an electronegatively-substituted iron porphyrin complex in aprotic solvent
Lee, YJ
Goh, YM
Han, SY
Kim, C
Nam, W
CHEMISTRY LETTERS, 1998, (08) : 837 - 838
[27] Active sites and mechanisms of bioinspired oxidation with H2O2, catalyzed by non-heme Fe and related Mn complexes
Bryliakov, Konstantin P.
Talsi, Evgenii P.
COORDINATION CHEMISTRY REVIEWS, 2014, 276 : 73 - 96
[28] Conflicting Role of Water in the Activation of H2O2 and the Formation and Reactivity of Non-Heme FeIII-OOH and FeIII-O-FeIII Complexes at Room Temperature
Padamati, Sandeep K.
Draksharapu, Apparao
Unjaroen, Duenpen
Browne, Wesley R.
INORGANIC CHEMISTRY, 2016, 55 (09) : 4211 - 4222
[29] First success of catalytic epoxidation of olefins by an electron-rich iron(III) porphyrin complex and H2O2:: imidazole effect on the activation of H2O2 by iron porphyrin complexes in aprotic solvent
Nam, W
Lee, HJ
Oh, SY
Kim, C
Jang, HG
JOURNAL OF INORGANIC BIOCHEMISTRY, 2000, 80 (3-4) : 219 - 225
[30] Insight into the chemoselective aromatic vs. side-chain hydroxylation of alkylaromatics with H2O2 catalyzed by a non-heme imine-based iron complex
Ticconi, Barbara
Capocasa, Giorgio
Cerrato, Andrea
Di Stefano, Stefano
Lapi, Andrea
Marincioni, Beatrice
Olivo, Giorgio
Lanzalunga, Osvaldo
CATALYSIS SCIENCE & TECHNOLOGY, 2021, 11 (01) : 171 - 178

← 1 2 3 4 5 →