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

[31] Theoretical Investigation on Reaction Mechanism of H2O2 Dismutation Catalyzed by a Non-heme Tetraaza Annulene Complex [Fe(III)TMTAA]
Zhang Ying
Wang Xin
Li Laicai
ACTA CHIMICA SINICA, 2010, 68 (07) : 633 - 640
[32] Hydroperoxidation of methane and other alkanes with H2O2 catalyzed by a dinuclear iron complex and an amino acid
Nizova, GV
Krebs, B
Süss-Fink, G
Schindler, S
Westerheide, L
Cuervo, LG
Shul'pin, GB
TETRAHEDRON, 2002, 58 (45) : 9231 - 9237
[33] Substrate-Specific Coupling of O2 Activation to Hydroxylations of Aromatic Compounds by Rieske Non-heme Iron Dioxygenases
Pati, Sarah G.
Bopp, Charlotte E.
Kohler, Hans-Peter E.
Hofstetter, Thomas B.
ACS CATALYSIS, 2022, 12 (11): : 6444 - 6456
[34] Iron-substituted SBA-15 microparticles: a peroxidase-like catalyst for H2O2 detection
Liu, Sen
Tian, Jingqi
Wang, Lei
Luo, Yonglan
Chang, Guohui
Sun, Xuping
ANALYST, 2011, 136 (23) : 4894 - 4897
[35] Iron Tetrasulfonatophthalocyanine-Catalyzed Starch Oxidation Using H2O2: Interplay between Catalyst Activity, Selectivity, and Stability
Genuino, Homer C.
Meinds, Tim G.
Broekman, J. O. P.
Staal, Marcel
Brinksma, Jelle
Wielema, Thomas
Picchioni, Francesco
Browne, Wesley R.
Deuss, Peter J.
Heeres, Hero J.
ACS OMEGA, 2021, 6 (21): : 13847 - 13857
[36] Rates of mitochondrial H2O2 production and non-heme iron contents in selected tissues from cold- and warm-acclimated striped bass (Morone saxatilis)
Wheeler, M. S.
Kelley, K.
Tapley, D. W.
Crockett, E. L.
INTEGRATIVE AND COMPARATIVE BIOLOGY, 2011, 51 : E265 - E265
[37] Olefin Epoxidation Catalyzed by Titanium-Salalen Complexes: Synergistic H2O2 Activation by Dinuclear Ti Sites, Ligand H-Bonding, and π-Acidity
Engler, Hauke
Lansing, Markus
Gordon, Christopher P.
Neudoerfl, Joerg-M
Schaefer, Mathias
Schloerer, Nils E.
Coperet, Christophe
Berkessel, Albrecht
ACS CATALYSIS, 2021, 11 (06): : 3206 - 3217
[38] A novel heteropolyanion-based amino-containing cross-linked ionic copolymer catalyst for epoxidation of alkenes with H2O2
Leng, Yan
Zhang, Weijie
Wang, Jun
Jiang, Pingping
APPLIED CATALYSIS A-GENERAL, 2012, 445 : 306 - 311
[39] Direct Selective Oxidative Functionalization of C-H Bonds with H2O2: Mn-Aminopyridine Complexes Challenge the Dominance of Non-Heme Fe Catalysts
Ottenbacher, Roman V.
Talsi, Evgenii P.
Bryliakov, Konstantin P.
MOLECULES, 2016, 21 (11):
[40] Highly efficient CuCr-MMO catalyst for a base-free styrene epoxidation with H2O2 as the oxidant: synergistic effect between Cu and Cr
Wang, Qian
Liang, Xiao
Bi, Ruxia
Liu, Yanan
He, Yufei
Feng, Junting
Li, Dianqing
DALTON TRANSACTIONS, 2019, 48 (43) : 16402 - 16411

← 1 2 3 4 5 →