Asymmetric oxidation of sulfides with H2O2 catalyzed by titanium complexes with aminoalcohol derived Schiff bases

被引:50
作者
Bryliakov, Konstantin P. [1 ]
Talsi, EvIrenii P. [1 ]
机构
[1] Russian Acad Sci, Siberian Branch, Boreskov Inst Catalysis, Novosibirsk 630090, Russia
基金
俄罗斯基础研究基金会;
关键词
asymmetric catalysis; H2O2; sulfoxides; chiral Schiff bases; titanium complexes;
D O I
10.1016/j.molcata.2006.09.038
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
Sulfoxidation catalysts generated in situ from titanium(IV) isopropoxide and enantiopure Schiff bases promote the enantioselective oxidation of alkyl aryl sulfides to the corresponding sulfoxides at low catalyst loadings (< 1 mol%), 30% aqueous hydrogen peroxide being the terminal oxidant. Upon screening of several ligands derived from beta-aminoalcohols and salicylaldehydes, a catalyst affording sulfoxides with over 90% chemoselectivity and up to 60% ee was found, and the kinetics of the catalytic reaction was analyzed by H-1 NMR. (c) 2006 Elsevier B.V. All rights reserved.
引用
收藏
页码:280 / 287
页数:8
相关论文
共 50 条
[1]  
[Anonymous], CATALYTIC ASYMMETRIC
[2]   A FURTHER STUDY OF EXO- AND ENDO-2-CARBO-T-BUTYLPEROXYNORBORNANES [J].
BARTLETT, PD ;
MCBRIDE, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (08) :1727-&
[3]  
Bolm C, 1995, ANGEW CHEM INT EDIT, V34, P2640
[4]  
Bolm C, 1998, SYNLETT, P1327
[5]   Copper- and vanadium-catalyzed asymmetric oxidations [J].
Bolm, C ;
Schlingloff, G ;
Bienewald, F .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1997, 117 (1-3) :347-350
[6]  
Bolm C., 1995, ANGEW CHEM, V107, P2883
[7]   Enantioselective Ti(IV) sulfoxidation catalysts-bearing C3-symmetric trialkanolamine ligands:: Solution speciation by 1H NMR and ESI-MS analysis [J].
Bonchio, M ;
Licini, G ;
Modena, G ;
Bortolini, O ;
Moro, S ;
Nugent, WA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (26) :6258-6268
[8]   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
[9]  
Bryliakov K. P., 2004, ANGEW CHEM, V116, P5340
[10]   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