Diastereoselective conversion of sulfides into sulfoxides. 1,5- and 1,6-asymmetric induction

被引：36

作者：

Bower, JF

Martin, CJ

Rawson, DJ

Slawin, AMZ

Williams, JMJ

机构：

[1] LOUGHBOROUGH UNIV TECHNOL,DEPT CHEM,LOUGHBOROUGH LE11 3TU,LEICS,ENGLAND

[2] PFIZER LTD,CENT RES,DEPT DISCOVERY CHEM,SANDWICH CT13 9NJ,KENT,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1996年 / 04期

关键词：

D O I：

10.1039/p19960000333

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The diastereoselective oxidation of sulfides into sulfoxides has been achieved with enantiomerically pure dihydrooxazole auxiliaries. When an additional hydroxymethyl substituent is present, diastereocontrol is very high and 1,5-asymmetric induction has been achieved with up to 96:4 selectivity, and 1,6-asymmetric induction has been achieved with up to 97: 3 selectivity in the absence of any additional chiral agents.

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页码：333 / 342

页数：10

相关论文

共 32 条

[1] THIANTHRENE 5-OXIDE (SSO) AS A MECHANISTIC PROBE OF THE ELECTROPHILIC CHARACTER IN THE OXYGEN-TRANSFER BY DIOXIRANES [J].

ADAM, W ;

GOLSCH, D .

CHEMISCHE BERICHTE, 1994, 127 (06) :1111-1113

[2] PREPARATION OF NOVEL SULFUR AND PHOSPHORUS-CONTAINING OXAZOLINES AS LIGANDS FOR ASYMMETRIC CATALYSIS [J].

ALLEN, JV ;

DAWSON, GJ ;

FROST, CG ;

WILLIAMS, JMJ ;

COOTE, SJ .

TETRAHEDRON, 1994, 50 (03) :799-808

[3] ENANTIOSELECTIVE PALLADIUM-CATALYZED ALLYLIC SUBSTITUTION - ELECTRONIC AND STERIC EFFECTS OF THE LIGAND [J].

ALLEN, JV ;

BOWER, JF ;

WILLIAMS, JMJ .

TETRAHEDRON-ASYMMETRY, 1994, 5 (10) :1895-1898

[4] BENZYL METHYL (S)-2-(P-TOLYLSULFINYL)MALEATE - AN EFFICIENT DIENOPHILE FOR THE ENANTIOSELECTIVE SYNTHESIS OF CYCLOHEXADIENES [J].

ALONSO, I ;

CARRETERO, JC ;

RUANO, JLG .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (12) :3231-3232

[5] OPTICALLY ACTIVE SULFOXIDES . SYNTHESIS + ROTATORY DISPERSION OF SOME DIARYL SULFOXIDES [J].

ANDERSEN, KK ;

FOLEY, JW ;

GAFFIELD, W ;

PAPANIKOLAU, NE ;

PERKINS, RI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (24) :5637-+

[6] POWERFUL DIENOPHILES FOR ASYMMETRIC DIELS-ALDER REACTIONS - ALPHA-(2-EXO-HYDROXY-10-BORNYLSULFINYL)MALEIMIDES [J].

ARAI, Y ;

MATSUI, M ;

KOIZUMI, T ;

SHIRO, M .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (06) :1983-1985

[7] SYNTHESIS OF OPTICALLY-ACTIVE BIS(2-OXAZOLINES) - CRYSTAL-STRUCTURE OF A 1,2-BIS(2-OXAZOLINYL)BENZENE.ZNCL2 COMPLEX [J].

BOLM, C ;

WEICKHARDT, K ;

ZEHNDER, M ;

RANFF, T .

CHEMISCHE BERICHTE, 1991, 124 (05) :1173-1180

[8] DIASTEREOSELECTIVE OXIDATION OF ARYLSULFIDES [J].

BOWER, JF ;

WILLIAMS, JMJ .

TETRAHEDRON LETTERS, 1994, 35 (38) :7111-7114

[9]

BREITSCHUH R, 1992, SYNTHESIS-STUTTGART, P1170

[10]

BROUGHAM P, 1987, SYNTHESIS-STUTTGART, P1015

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