Highly enantioselective iron-catalyzed sulfide oxidation with aqueous hydrogen peroxide under simple reaction conditions

被引：211

作者：

Legros, J ^{[1
]}

Bolm, C ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52056 Aachen, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 32期

关键词：

asymmetric catalysis; iron; oxidation; peroxides; sulfoxides;

D O I：

10.1002/anie.200460236

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An attractive alternative to the currently existing methods for the metal-catalyzed oxidation of sulfides to sulfoxides is asymmetric iron-catalyzed oxidation with hydrogen peroxide as the terminal oxidant (see scheme). In the presence of a benzoic acid derivative, this simple process provides sulfoxides with up to 96% ee in moderate to good yields (up to 78%).

引用

页码：4225 / 4228

页数：4

共 50 条

[21] Titanium Catalyzed Enantioselective Oxidation of Thioethers with Hydrogen Peroxide
Bryliakov, Konstantin P.
MINI-REVIEWS IN ORGANIC CHEMISTRY, 2014, 11 (01) : 87 - 96
[22] STABILIZATION OF IRON-CATALYZED HYDROGEN-PEROXIDE DECOMPOSITION BY MAGNESIUM
ABBOT, J
BROWN, DG
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1990, 68 (09): : 1537 - 1543
[23] COBALT INHIBITION OF IRON-CATALYZED HYDROGEN PEROXIDE DECOMPOSITION OF RIBOFLAVIN
WELKIE, GW
BIOCHIMICA ET BIOPHYSICA ACTA, 1968, 158 (03) : 479 - &
[24] Highly Enantioselective Copper- and Iron-Catalyzed Intramolecular Cyclopropanation of Indoles
Xu, Huan
Li, Yi-Pan
Cai, Yan
Wang, Guo-Peng
Zhu, Shou-Fei
Zhou, Qi-Lin
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (23) : 7697 - 7700
[25] Highly enantioselective iron-catalyzed synthesis of oxaheterocycles via reduction of ω-haloketones
Blasius, Clemens
Vasilenko, Vladislav
Gade, Lutz
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
[26] IRON-CATALYZED OXIDATION OF UROPORPHYRIN UNDER ATMOSPHERIC OXYGEN
MUKERJI, SK
PIMSTONE, NR
HEPATOLOGY, 1988, 8 (05) : 1412 - 1412
[27] Development of a general and efficient iron-catalyzed epoxidation with hydrogen peroxide as oxidant
Bitterlich, Bianca
Anilkumar, Gopinathan
Gelalcha, Feyissa Gadissa
Spilker, Bjoern
Grotevendt, Anne
Jackstell, Ralf
Tse, Man Kin
Beller, Matthias
CHEMISTRY-AN ASIAN JOURNAL, 2007, 2 (04) : 521 - 529
[28] Iron-catalyzed asymmetric epoxidation of aromatic alkenes using hydrogen peroxide
Gelalcha, Feyissa Gadissa
Bitterlich, Bianca
Anilkumar, Gopinathan
Tse, Man Kin
Beller, Matthias
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (38) : 7293 - 7296
[29] Asymmetric oxidation catalysis by a chiral Al(salalen) complex: Highly enantioselective oxidation of sulfides with aqueous hydrogen peroxide
Yamaguchi, Tetsufumi
Matsumoto, Kazuhiro
Saito, Bunnai
Katsuki, Tsutomu
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (25) : 4729 - 4731
[30] Iron-catalyzed sulfonylimine synthesis under neutral conditions
Wu, Xiao-Feng
Vovard-Le Bray, Chloe
Bechki, Lazhar
Darcel, Christophe
TETRAHEDRON, 2009, 65 (36) : 7380 - 7384

← 1 2 3 4 5 →