Vanadium-catalyzed enantioselective sulfoxidation of methyl aryl sulfides with hydrogen peroxide as terminal oxidant

被引：1

作者：

Ohta, C ^{[1
]}

Shimizu, H ^{[1
]}

Kondo, A ^{[1
]}

Katsuki, T ^{[1
]}

机构：

[1] Kyushu Univ 33, Grad Sch, Fac Sci, Dept Chem,Higashi Ku, Fukuoka 8128581, Japan

来源：

SYNLETT | 2002年 / 01期

关键词：

asymmetric catalysis; chiral vanadium complex; Schiff base; enantioselective sulfoxidation; hydrogen peroxide;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral vanadium complex prepared in situ from VO(acac)(2) and Schiff base 9 was found to be an efficient catalyst for oxidation of various methyl aryl sulfides with hydrogen peroxide as terminal oxidant, For example, oxidation of methyl 2-naphthyl sulfide using a VO(acac)(2), 9. and hydrogen peroxide system proceeded with high enantioselectivity of 93% ee as well as acceptable chemical yield.

引用

页码：161 / 163

页数：3

共 50 条

[31] REACTIVITY AND SELECTIVITY IN THE OXIDATION OF ARYL METHYL SULFIDES AND SULFOXIDES BY HYDROGEN-PEROXIDE MEDIATED BY ACETONITRILE
BETHELL, D
GRAHAM, AE
HEER, JP
MARKOPOULOU, O
PAGE, PCB
PARK, BK
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1993, (11): : 2161 - 2162
[32] Copper-Catalyzed Oxidative -Ketoacylations of Sulfoximines with Aryl Methyl Ketones and Dioxygen as Terminal Oxidant
Cheng, Hanchao
Bolm, Carsten
SYNLETT, 2016, 27 (05) : 769 - 772
[33] Vanadium-catalyzed asymmetric oxidation of α-hydroxy esters using molecular oxygen as stoichlometric oxidant
Radosevich, AT
Musich, C
Toste, FD
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (04) : 1090 - 1091
[34] Titanium-catalyzed, asymmetric sulfoxidation of alkyl aryl sulfides with optically active hydroperoxides
Adam, W
Korb, MN
Roschmann, KJ
Saha-Möller, CR
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (10): : 3423 - 3428
[35] Cationic Co(III)(salen)-catalyzed enantioselective Baeyer-Villiger oxidation of 3-arylcyclobutanones using hydrogen peroxide as a terminal oxidant
Uchida, T
Katsuki, T
TETRAHEDRON LETTERS, 2001, 42 (39) : 6911 - 6914
[36] Intramolecular Aminoazidation of Unactivated Terminal Alkenes by Palladium-Catalyzed Reactions with Hydrogen Peroxide as the Oxidant
Foschi, Francesca
Loro, Camilla
Sala, Roberto
Oble, Julie
Lo Presti, Leonardo
Beccalli, Egle M.
Poli, Giovanni
Broggini, Gianluigi
ORGANIC LETTERS, 2020, 22 (04) : 1402 - 1406
[37] Chiral Calcium-Catalyzed Asymmetric Epoxidation Reactions Using Hydrogen Peroxide as the Terminal Oxidant
Yamashita, Yasuhiro
Macor, Joseph Alexander
Fushimi, Seiya
Tsubogo, Tetsu
Kobayashi, Shu K
CHEMICAL & PHARMACEUTICAL BULLETIN, 2018, 66 (09) : 847 - 850
[38] Metal-catalyzed asymmetric sulfoxidation, epoxidation and hydroxylation by hydrogen peroxide
Srour, Hassan
Le Maux, Paul
Chevance, Soizic
Simonneaux, Gerard
COORDINATION CHEMISTRY REVIEWS, 2013, 257 (21-22) : 3030 - 3050
[39] Substituent effects and mechanism elucidation of enantioselective sulfoxidation catalyzed by vanadium Schiff base complexes
Zeng, QL
Wang, HQ
Weng, W
Lin, WS
Gao, YX
Huang, XT
Zhao, YF
NEW JOURNAL OF CHEMISTRY, 2005, 29 (09) : 1125 - 1127
[40] Highly selective sulfoxidation of allylic and vinylic sulfides by hydrogen peroxide using a flavin as catalyst
Lindén, AA
Krüger, L
Bäckvall, JE
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (15): : 5890 - 5896

← 1 2 3 4 5 →