DIASTEREOSELECTIVE OXIDATION OF ARYLSULFIDES

被引:16
作者
BOWER, JF [1 ]
WILLIAMS, JMJ [1 ]
机构
[1] LOUGHBOROUGH UNIV TECHNOL,DEPT CHEM,LOUGHBOROUGH LE11 3TU,LEICS,ENGLAND
关键词
D O I
10.1016/0040-4039(94)88239-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Arylsulfides containing an enantiomerically pure oxazoline in the ortho-position have been oxidised to the corresponding sulfoxides with a variety of reagents. When the oxazoline unit contains a 4-hydroxymethyl group, good levels of diastereocontrol have been obtained using mCPBA (96:4) or t-butylhydroperoxide and titanium tetraisopropoxide (97:3) as the oxidant. This diastereocontrol provides an effective example of 1,6-asymmetric induction.
引用
收藏
页码:7111 / 7114
页数:4
相关论文
共 28 条
[1]   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
[2]   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
[3]   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-+
[4]   ASYMMETRIC INDUCTION TO SULFUR ATOM - STEREOCONTROLLED S-OXIDATION OF THIAZOLIDINES [J].
ANDO, W ;
HUANG, L .
TETRAHEDRON LETTERS, 1986, 27 (29) :3391-3394
[5]   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
[6]   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
[7]  
BREITSCHUH R, 1992, SYNTHESIS-STUTTGART, P1170
[8]  
BROUGHAM P, 1987, SYNTHESIS-STUTTGART, P1015
[9]   RECOVERABLE CHIRAL SULFOXIDES FOR ASYMMETRIC-SYNTHESIS - PREPARATION, REGENERATION AND APPLICATION TO THE ASYMMETRIC ALDOL REACTION [J].
BUTLIN, RJ ;
LINNEY, ID ;
CRITCHER, DJ ;
MAHON, MF ;
MOLLOY, KC ;
WILLS, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (14) :1581-1589
[10]   DIPHENYLTHIIRENE 1-OXIDE - SYNTHESIS, CHARACTERIZATION, AND REACTIVITY [J].
CARPINO, LA ;
CHEN, HW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (02) :390-394