Iron-catalyzed asymmetric epoxidation of aromatic alkenes using hydrogen peroxide

被引：193

作者：

Gelalcha, Feyissa Gadissa ^{[1
]}

Bitterlich, Bianca ^{[1
]}

Anilkumar, Gopinathan ^{[1
]}

Tse, Man Kin ^{[1
]}

Beller, Matthias ^{[1
]}

机构：

[1] Univ Rostock eV, Leibniz Inst Katalyse, D-18059 Rostock, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 38期

关键词：

asymmetric catalysis; epoxidation; hydrogen peroxide; iron;

D O I：

10.1002/anie.200701235

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Ironing out the wrinkles: Highly enantioselective catalytic asymmetric epoxidation of aromatic alkenes with hydrogen peroxide proceeds smoothly in the presence of a catalyst system consisting of ferric hexahydrate, pyridine-2,6-dicarboxylic acid, and the novel chiral ligand 1 in 2-methylbutane-2-ol solvent at room temperature within 1 h (see scheme; Bn = benzyl). © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：7293 / 7296

页数：4

共 37 条

[11] Poly(ethylene glycol) (PEG) as a reusable solvent medium for organic synthesis. Application in the Heck reaction [J].

Chandrasekhar, S ;

Narsihmulu, C ;

Sultana, SS ;

Reddy, NR .

ORGANIC LETTERS, 2002, 4 (25) :4399-4401

[12]

Cheng QF, 2005, CHINESE CHEM LETT, V16, P1467

[13] Asymmetric epoxidation of terminal alkenes with hydrogen peroxide catalyzed by pentafluorophenyl PtII complexes [J].

Colladon, Marco ;

Scarso, Alessandro ;

Sgarbossa, Paolo ;

Michelin, Rino A. ;

Strukul, Giorgio .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (43) :14006-14007

[14] 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

[15]

Francis MB, 1999, ANGEW CHEM INT EDIT, V38, P937, DOI 10.1002/(SICI)1521-3773(19990401)38:7<937::AID-ANIE937>3.0.CO

[16]

2-O

[17]

FURUHASHI K, 1992, CHIRALITY IND, P167

[18] Novel catalytic kinetic resolution of racemic epoxides to allylic alcohols [J].

Gayet, A ;

Bertilsson, S ;

Andersson, PG .

ORGANIC LETTERS, 2002, 4 (22) :3777-3779

[19] Fluorinated chiral secondary amines as catalysts for epoxidation of olefins with oxone [J].

Ho, CY ;

Chen, YC ;

Wong, MK ;

Yang, D .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (03) :898-906

[20]

Jacobsen E. N., 1999, COMPREHENSIVE ASYMME, V2, P649

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