Asymmetric oxidation of sulfides with hydrogen peroxide catalyzed by a vanadium complex of a new chiral NOO-ligand

被引：19

作者：

Liu, Haibin ^{[1
]}

Wang, Mei ^{[1
]}

Wang, Yu ^{[1
]}

Wang, Ying ^{[1
]}

Sun, Hui ^{[1
]}

Sun, Licheng ^{[1
,2
]}

机构：

[1] Dalian Univ Technol, State Key Lab Fine Chem, DUT KTH Joint Educ & Res Ctr Mol Devices, Dalian 116012, Peoples R China

[2] Royal Inst Technol, Dept Chem, S-10044 Stockholm, Sweden

来源：

CATALYSIS COMMUNICATIONS | 2009年 / 11卷 / 04期

关键词：

Asymmetric oxidation; Chiral NOO-ligand; Chiral sulfoxide; Sulfoxidation; Vanadium catalyst; ENANTIOSELECTIVE OXIDATION; SULFOXIDATION;

D O I：

10.1016/j.catcom.2009.10.017

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A new chiral NOO-tridentate ligand (8R)-2-(2-hydroxyphenyl)-4-methyl-5,6,7.8-tetrahydro-quinolin-8-ol (1) bearing a rigid tetrahydroquinoline framework was prepared and applied in the vanadium-catalyzed asymmetric oxidation of aryl methyl sulfides with H2O2 as oxidant. Less toxic acetone was found to be the proper solvent for the enantioselective oxidation of sulfides. Under the optimal condition, the asymmetric oxidation of aryl methyl sulfides in acetone catalyzed by VO(acac)(2)/1 at 0 degrees C gives good to high yields (80-95%) of sulfoxides with enantioselectivity up to 77% ee. (C) 2009 Elsevier B.V. All rights reserved.

引用

页码：294 / 297

页数：4

共 29 条

[1] Role of sulfur chirality in the chemical processes of biology [J].

Bentley, R .

CHEMICAL SOCIETY REVIEWS, 2005, 34 (07) :609-624

[2]

Bolm C, 1995, ANGEW CHEM INT EDIT, V34, P2640

[3] The first chiral zirconium(IV) catalyst for highly stereoselective sulfoxidation [J].

Bonchio, M ;

Licini, G ;

Di Furia, F ;

Mantovani, S ;

Modena, G ;

Nugent, WA .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (04) :1326-1330

[4] Fluorous biphasic oxidation of sulfides catalysed by (salen)manganese(III) complexes [J].

Cavazzini, M ;

Pozzi, G ;

Quici, S ;

Shepperson, I .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2003, 204 :433-441

[5] Asymmetric synthesis of esomeprazole [J].

Cotton, H ;

Elebring, T ;

Larsson, M ;

Li, L ;

Sörensen, H ;

von Unge, S .

TETRAHEDRON-ASYMMETRY, 2000, 11 (18) :3819-3825

[6] Catalytic asymmetric oxidation of aryl sulfides with a Ti/H2O/(R,R)-diphenylethane-1,2-diol complex:: a versatile and highly enantioselective oxidation protocol [J].

Donnoli, MI ;

Superchi, S ;

Rosini, C .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) :9392-9395

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

Fernández, I ;

Khiar, N .

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

[8]

Franklin A.D., 1992, J AM CHEM SOC, V114, P1428

[9] ASYMMETRIC HYDROXYLATION, EPOXIDATION, AND SULFOXIDATION CATALYZED BY VAULTED BINAPHTHYL METALLOPORPHYRINS [J].

GROVES, JT ;

VISKI, P .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11) :3628-3634

[10] Development of a preparative-scale asymmetric synthesis of (R)-p-tolyl methyl sulfoxide for use in a one-pot synthesis of a drug intermediate containing a trifluoromethyl-substituted alcohol functionality [J].

Han, Zhengxu ;

Song, Jinhua J. ;

Yee, Nathan K. ;

Xu, Yibo ;

Tang, Wenjun ;

Reeves, Jonathan T. ;

Tan, Zhulin ;

Wang, Xiao-Jun .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (03) :605-608

← 1 2 3 →