HIGHLY ENANTIOSELECTIVE OXIDATION OF ARYL BENZYL SULFIDES

被引：3

作者：

Cardellicchio, Cosimo ^{[1
]}

Capozzi, Maria Annunziata M. ^{[2
]}

Centrone, Caterina

Naso, Francesco

机构：

[1] Univ Bari, CNR ICCOM, Dipartimento Chim, I-70125 Bari, Italy

[2] Univ Foggia, Dipartimento Sci Agroambientali Chim & Difesa Veg, Foggia, Italy

来源：

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 2011年 / 186卷 / 05期

关键词：

Hydrobenzoin; oxidation mechanism; sulfoxide; titanium complex; CARBON SUBSTITUTION-REACTIONS; DIALKYL SULFOXIDES; SULFINYL GROUP; LEAVING GROUPS; ROUTE;

D O I：

10.1080/10426507.2010.529856

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Enantiopure aryl benzyl sulfoxides were easily obtained by an enantioselective oxidation of the corresponding sulfides with tert-butyl hydroperoxide in the presence of a complex between titanium and (S, S)- or (R, R)-hydrobenzoin. Theoretical and experimental investigations confirmed that these aryl benzyl sulfides represent an ideal substrate for the asymmetric oxidation system.

引用

页码：1193 / 1195

页数：3

共 12 条

[1]

[Anonymous], COMPREHENSIVE ASYMME

[2] Enantioselective routes to Sulfoxides based upon the use of carbanionic leaving groups [J].

Capozzi, MAM ;

Cardellicchio, C ;

Naso, F .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (09) :1855-1863

[3] Enantioselective catalytic oxidation of (arylthio)- or (alkylthio)methylphosphonates as a route to enantiomeric pure aryl alkyl or dialkyl sulfoxides [J].

Capozzi, MAM ;

Cardellicchio, C ;

Fracchiolla, G ;

Naso, F ;

Tortorella, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (19) :4708-4709

[4] A straightforward enantioselective route to dialkyl sulfoxides based upon two carbon-for-carbon substitution reactions on the sulfinyl group [J].

Capozzi, MAM ;

Cardellicchio, C ;

Naso, F ;

Rosito, V .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (21) :7289-7294

[5] Substituted benzene anions as leaving groups in the reaction of sulfinyl derivatives with grignard reagents: A new and convenient route to dialkyl sulfoxides in high enantiomeric purity [J].

Capozzi, MAM ;

Cardellicchio, C ;

Naso, F ;

Tortorella, P .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (09) :2843-2846

[6] Enantioselective routes to sulfoxides based upon carbon-for-carbon substitution reactions on the sulfinyl group [J].

Cardellicchio, C ;

Naso, F ;

Capozzi, MAM .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2005, 180 (5-6) :1161-1170

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

Fernández, I ;

Khiar, N .

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

[8] Applications of catalytic asymmetric sulfide oxidations to the syntheses of biologically active sulfoxides [J].

Legros, J ;

Dehli, JR ;

Bolm, C .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (01) :19-31

[9] Asymmetric synthesis of Sulindac esters by enantioselective sulfoxidation in the presence of chiral titanium complexes [J].

Naso, Francesco ;

Cardellicchio, Cosimo ;

Affortunato, Francesco ;

Capozzi, Maria Annunziata M. .

TETRAHEDRON-ASYMMETRY, 2006, 17 (23) :3226-3229

[10] A Combined Theoretical and Experimental Investigation on the Enantioselective Oxidation of Aryl Benzyl Sulfides in the Presence of a Chiral Titanium Catalyst [J].

Naso, Francesco ;

Capozzi, Maria Annunziata M. ;

Bottoni, Andrea ;

Calvaresi, Matteo ;

Bertolasi, Valerio ;

Capitelli, Francesco ;

Cardellicchio, Cosimo .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (48) :13417-13426

← 1 2 →