Enantioselective oxidation of sulfides with H2O2 catalyzed by a pre-formed manganese complex

被引：30

作者：

Dai, Wen ^{[1
,2
]}

Li, Guosong ^{[1
]}

Wang, Lianyue ^{[1
]}

Chen, Bo ^{[1
,2
]}

Shang, Sensen ^{[1
,2
]}

Lv, Ying ^{[1
]}

Gao, Shuang ^{[1
]}

机构：

[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian Natl Lab Clean Energy, Dalian 116023, Peoples R China

[2] Univ Chinese Acad Sci, Beijing 10049, Peoples R China

来源：

RSC ADVANCES | 2014年 / 4卷 / 87期

关键词：

ALBENDAZOLE SULFOXIDE ENANTIOMERS; EFFICIENT ASYMMETRIC OXIDATION; HYDROGEN-PEROXIDE; ARYL SULFIDES; CHIRALITY; EPOXIDATION; THIOETHERS; SEPARATION; LIGANDS; OLEFINS;

D O I：

10.1039/c4ra09832c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A facile and environmentally friendly method is presented for the asymmetric oxidation of sulfides with H2O2, utilizing a pre-formed manganese complex. Just in the presence of a low catalytic amount of carboxylic acid (CA), a variety of sulfide substrates, including aryl alkyl, aryl benzyl and cyclic sulfides, reacted to form chiral sulfoxides in high yields (up to 95%) and excellent enantioselectivities (>99% ee) under mild conditions. Moreover, the practical utility of the method has been demonstrated by the synthesis of esomeprazole and albendazole sulfoxide (ABZO).

引用

页码：46545 / 46554

页数：10

共 63 条

[1] Practical oxidation of sulfides to sulfones by H2O2 catalysed by titanium catalyst [J].

Al-Maksoud, Walid ;

Daniele, Stephane ;

Sorokin, Alexander B. .

GREEN CHEMISTRY, 2008, 10 (04) :447-451

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

Bentley, R .

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

[3]

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

[4] Merrifield resin supported peroxomolybdenum(VI) compounds: recoverable heterogeneous catalysts for the efficient, selective and mild oxidation of organic sulfides with H2O2 [J].

Boruah, Jeena Jyoti ;

Das, Siva Prasad ;

Ankireddy, Seshadri Reddy ;

Gogoi, Sandhya Rani ;

Islam, Nashreen S. .

GREEN CHEMISTRY, 2013, 15 (10) :2944-2959

[5]

Bryliakov K.P., 2004, Angew. Chem, V116, P5340

[6] Iron-catalyzed oxidation of thioethers by iodosylarenes: Setereoselectivity and reaction mechanism [J].

Bryliakov, Konstantin P. ;

Talsi, Evgenii P. .

CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (28) :8045-8050

[7] Enantiopure sulfoxides: recent applications in asymmetric synthesis [J].

Carmen Carreno, M. ;

Hernandez-Torres, Gloria ;

Ribagorda, Maria ;

Urbano, Antonio .

CHEMICAL COMMUNICATIONS, 2009, (41) :6129-6144

[8] A molybdenum based metallomicellar catalyst for controlled and selective sulfoxidation reactions in aqueous medium [J].

Chakravarthy, Rajan Deepan ;

Ramkumar, Venkatachalam ;

Chand, Dillip Kumar .

GREEN CHEMISTRY, 2014, 16 (04) :2190-2196

[9] 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

[10] Asymmetric Epoxidation with H2O2 by Manipulating the Electronic Properties of Non-heme Iron Catalysts [J].

Cusso, Olaf ;

Garcia-Bosch, Isaac ;

Ribas, Xavi ;

Lloret-Fillol, Julio ;

Costas, Miquel .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (39) :14871-14878

← 1 2 3 4 5 6 7 →