Asymmetric oxidation catalysis by a chiral Al(salalen) complex: Highly enantioselective oxidation of sulfides with aqueous hydrogen peroxide

被引：75

作者：

Yamaguchi, Tetsufumi ^{[1
]}

Matsumoto, Kazuhiro ^{[1
]}

Saito, Bunnai ^{[1
]}

Katsuki, Tsutomu ^{[1
]}

机构：

[1] Kyushu Univ, Grad Sch, Fac Sci, Dept Chem, Fukuoka 812, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 25期

关键词：

aluminum; asymmetric catalysis; hydrogen peroxide; oxidation; sulfides;

D O I：

10.1002/anie.200700792

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Not afraid to get wet: Aluminum(salalen) complexes were found to be water compatible and therefore suitable catalysts for asymmetric oxidation with aqueous hydrogen peroxide. A variety of sulfides underwent the title reaction in the presence of the aluminum(salalen) complex shown to the give the desired sulfoxides with high to excellent enantioselectivity (see scheme; Bn = benzyl). © 2007 Wiley-VCH Verlag GmbH &. Co. KGaA.

引用

页码：4729 / 4731

页数：3

共 57 条

[1]

[Anonymous], ANGEW CHEM

[2] Regioselective catalytic asymmetric reaction of Horner-Wadsworth-Emmons reagents with enones: The odyssey of chiral aluminum catalysts [J].

Arai, T ;

Sasai, H ;

Yamaguchi, K ;

Shibasaki, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (02) :441-442

[3] Catalytic enantioselective conjugate addition of indoles to simple α,β-unsaturated ketones [J].

Bandini, M ;

Fagioli, M ;

Melchiorre, P ;

Melloni, A ;

Umani-Ronchi, A .

TETRAHEDRON LETTERS, 2003, 44 (31) :5843-5846

[4] Catalytic enantioselective oxidation of sulfides and disulfides by a chiral complex of bis-hydroxamic acid and molybdenum [J].

Basak, A ;

Barlan, AU ;

Yamamoto, H .

TETRAHEDRON-ASYMMETRY, 2006, 17 (04) :508-511

[5] Enantioselective oxidation of di-tert-butyl disulfide with a vanadium catalyst:: Progress toward mechanism elucidation [J].

Blum, SA ;

Bergman, RG ;

Ellman, JA .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (01) :150-155

[6]

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

[7] Vaulted biaryls: Efficient ligands for the aluminum-catalyzed asymmetric Baeyer-Villiger reaction [J].

Bolm, C ;

Frison, JC ;

Zhang, Y ;

Wulff, WD .

SYNLETT, 2004, (09) :1619-1621

[8] Chiral aluminum complexes as catalysts in asymmetric Baeyer-Villiger reactions of cyclobutanones [J].

Bolm, C ;

Beckmann, O ;

Palazzi, C .

CANADIAN JOURNAL OF CHEMISTRY, 2001, 79 (11) :1593-1597

[9] Influence of hydroperoxides on the enantioselectivity of metal-catalyzed asymmetric Baeyer-Villiger oxidation and epoxidation with chiral ligands [J].

Bolm, C ;

Beckmann, O ;

Kühn, T ;

Palazzi, C ;

Adam, W ;

Rao, PB ;

Saha-Möller, CR .

TETRAHEDRON-ASYMMETRY, 2001, 12 (17) :2441-2446

[10]

Bolm C., 1995, ANGEW CHEM, V107, P2883

← 1 2 3 4 5 6 →