Vanadium catalyzed enantioselective oxidation of sulfides:: easy transformation of bis(arylthio)alkanes into C2 symmetric chiral sulfoxides

被引：75

作者：

Skarzewski, J ^{[1
]}

Ostrycharz, E ^{[1
]}

Siedlecka, R ^{[1
]}

机构：

[1] Wroclaw Tech Univ, Inst Organ Chem Biochem & Biotechnol, PL-50370 Wroclaw, Poland

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 18期

关键词：

D O I：

10.1016/S0957-4166(99)00374-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A facile and selective method for the title transformation is described. The two-phase oxidation of bis-sulfides with hydrogen peroxide catalyzed by vanadium complex of chiral Schiff base leads to the corresponding chiral mono- and bis-sulfoxides. In the case of 1,2-bis(arylthio)ethanes the respective optically active bis-sulfoxides are formed in up to over 95% e.e. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：3457 / 3461

页数：5

共 26 条

[1] Studies on the asymmetric oxidation of ester derivatives of 1,3-dithiane-2-carboxylates. Asymmetric synthesis of trans-1,3-dithiane 1,3-dioxide [J].

Aggarwal, VK ;

Esquivel-Zamora, BN ;

Evans, GR ;

Jones, E .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (21) :7306-7310

[2] Nonlinear stereochemical effects in asymmetric reactions [J].

Avalos, M ;

Babiano, R ;

Cintas, P ;

Jimenez, JL ;

Palacios, JC .

TETRAHEDRON-ASYMMETRY, 1997, 8 (18) :2997-3017

[3] Synthesis of thiols, selenols, sulfides, selenides, sulfoxides, selenoxides, sulfones and selenones [J].

Baird, CP ;

Rayner, CM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (12) :1973-2003

[4] ENANTIOSELECTIVE OXIDATION OF THIOETHERS1 - AN EASY ROUTE TO ENANTIOPURE C-2 SYMMETRICAL BIS-METHYLSULFINYLBENZENES [J].

BENDAZZOLI, P ;

DIFURIA, F ;

LICINI, G ;

MODENA, G .

TETRAHEDRON LETTERS, 1993, 34 (18) :2975-2978

[5]

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

[6]

Bolm C, 1998, SYNLETT, P1327

[7] 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

[8] APPLICATIONS OF SULFOXIDES TO ASYMMETRIC-SYNTHESIS OF BIOLOGICALLY-ACTIVE COMPOUNDS [J].

CARRENO, MC .

CHEMICAL REVIEWS, 1995, 95 (06) :1717-1760

[9] Catalytic asymmetric oxidation of tert-butyl disulfide.: Synthesis of tert-butanesulfinamides, tert-butyl sulfoxides, and tert-butanesulfinimines [J].

Cogan, DA ;

Liu, GC ;

Kim, KJ ;

Backes, BJ ;

Ellman, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (32) :8011-8019

[10] ASSEMBLING SYNTHONS IN A CHIRAL FORM - EQUIVALENCE OF 6H,12H-DIBENZO[B,F][1,5]DITHIOCIN-S,S'-DIOXIDE TO 2 CHIRAL BENZYL UNITS [J].

COSSU, S ;

DELUCCHI, O ;

PIGA, E ;

LICINI, G .

TETRAHEDRON LETTERS, 1992, 33 (15) :2053-2054

← 1 2 3 →