Fe(salan)-catalyzed asymmetric oxidation of sulfides with hydrogen peroxide in water

被引：255

作者：

Egami, Hiromichi ^{[1
]}

Katsuki, Tsutomu ^{[1
]}

机构：

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 29期

关键词：

D O I：

10.1021/ja071916+

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new chiral Fe(salan) complex was synthesized, and it was found to serve as an efficient catalyst for asymmetric oxidation of sulfides using hydrogen peroxide in water without surfactant. Not only alkyl aryl sulfides but also various methyl alkyl sulfides were oxidized to the corresponding sulfoxides with high enantioselectivities up to 96% ee. It should be noted that the turnover number of complex 4 amounts to 8000.

引用

页码：8940 / +

页数：3

共 37 条

[1] Catalytic asymmetric ring opening of meso-epoxides with aromatic amines in water [J].

Azoulay, S ;

Manabe, K ;

Kobayashi, S .

ORGANIC LETTERS, 2005, 7 (21) :4593-4595

[2] Vanadium-catalyzed asymmetric oxidations [J].

Bolm, C .

COORDINATION CHEMISTRY REVIEWS, 2003, 237 (1-2) :245-256

[3] Iron-catalyzed reactions in organic synthesis [J].

Bolm, C ;

Legros, J ;

Le Paih, J ;

Zani, L .

CHEMICAL REVIEWS, 2004, 104 (12) :6217-6254

[4] Chiral scandium-catalysed enantioselective ring-opening of meso-epoxides with N-heterocycle, alcohol and thiol derivatives in water [J].

Boudou, Marine ;

Ogawa, Chikako ;

Kobayashi, Shu .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (18) :2585-2589

[5] Ligand-accelerated vanadium-catalysed epoxidation in water [J].

Bourhani, Z ;

Malkov, AV .

CHEMICAL COMMUNICATIONS, 2005, (36) :4592-4594

[6] HIGHLY ENANTIOSELECTIVE OXIDATION OF SULFIDES MEDIATED BY A CHIRAL TITANIUM COMPLEX [J].

BRUNEL, JM ;

DITER, P ;

DUETSCH, M ;

KAGAN, HB .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (24) :8086-8088

[7] Evidence for the formation of an iodosylbenzene(salen)iron active intermediate in a (salen)iron (III)-catalyzed asymmetric sulfide oxidation [J].

Bryliakov, KP ;

Talsi, EP .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5228-5230

[8] Vanadium-catalyzed sulfur oxidation/kinetic resolution in the synthesis of enantiomerically pure alkyl aryl sulfoxides [J].

Drago, C ;

Caggiano, L ;

Jackson, RFW .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (44) :7221-7223

[9] Recent developments in the synthesis and utilization of chiral sulfoxides [J].

Fernández, I ;

Khiar, N .

CHEMICAL REVIEWS, 2003, 103 (09) :3651-3705

[10] A heterogeneous silica-supported scandium/ionic liquid catalyst system for organic reactions in water [J].

Gu, Yanlong ;

Ogawa, Chikako ;

Kobayashi, Juta ;

Mori, Yuichiro ;

Kobayashi, Shu .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (43) :7217-7220

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