ASYMMETRIC OXIDATION OF SULFENYL SUBSTITUTED TRICARBONYL(ETA(6)-ARENE)CHROMIUM(0) COMPLEXES

被引:13
作者
GRIFFITHS, SL [1 ]
PERRIO, S [1 ]
THOMAS, SE [1 ]
机构
[1] IMPERIAL COLL SCI TECHNOL & MED,DEPT CHEM,LONDON SW7 2AY,ENGLAND
关键词
D O I
10.1016/0957-4166(94)80014-6
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Oxidation of sulfenyl substituted tricarbonyl(eta(6)-arene)chromium(0) complexes with Ti(OPri)(4) / diethyl tartrate / H2O / cumene hydroperoxide (2:4:2:1.3) gives sulfinyl substituted tricarbonyl(eta(6)- arene)chromium(0) complexes in 60-73% yield and 81-86% e.e. (29-60% yield and 90-greater than or equal to 95% e.e. after crystallisation); diethyl L-(+)-tartrate was shown to lead to complexes of R configuration.
引用
收藏
页码:545 / 548
页数:4
相关论文
共 25 条
  • [1] RESOLUTION AND ASYMMETRIC-SYNTHESIS OF ORTHO-SUBSTITUTED (BENZALDEHYDE)TRICARBONYLCHROMIUM COMPLEXES
    ALEXAKIS, A
    MANGENEY, P
    MAREK, I
    ROSEMUNCH, F
    ROSE, E
    SEMRA, A
    ROBERT, F
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (21) : 8288 - 8290
  • [2] [Anonymous], ADV MET ORG CHEM
  • [3] ASYMMETRIC DEPROTONATION AND COMPLEXATION REACTIONS MEDIATED BY CHIRAL KETALS AS A ROUTE TO ORTHO-DISUBSTITUTED (ETA-6-ARENE)CR(CO)3 COMPLEXES
    AUBE, J
    HEPPERT, JA
    MILLIGAN, ML
    SMITH, MJ
    ZENK, P
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (13) : 3563 - 3570
  • [4] THE DIASTEREOSELECTIVE FUNCTIONALIZATION OF ARENE TRICARBONYLCHROMIUM COMPLEXES CONTAINING A BENZYLIC HETEROATOM SUBSTITUENT
    BLAGG, J
    DAVIES, SG
    GOODFELLOW, CL
    SUTTON, KH
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (08): : 1805 - 1811
  • [5] STEREOSELECTIVE SYNTHESIS OF HOMOCHIRAL ALPHA SUBSTITUTED ORTHO-METHOXYBENZYL ALCOHOLS VIA NUCLEOPHILIC ADDITIONS TO KINETICALLY RESOLVED HOMOCHIRAL TRICARBONYL (ETA-6-ORTHO-ANISALDEHYDE)CHROMIUM(0)
    BROMLEY, LA
    DAVIES, SG
    GOODFELLOW, CL
    [J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (02) : 139 - 156
  • [6] CHEMISTRY OF OXAZIRIDINES .18. SYNTHESIS AND ENANTIOSELECTIVE OXIDATIONS OF THE [(8,8-DIHALOCAMPHORYL)SULFONYL]OXAZIRIDINES
    DAVIS, FA
    WEISMILLER, MC
    MURPHY, CK
    REDDY, RT
    CHEN, BC
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (26) : 7274 - 7285
  • [7] CHIRAL T-BUTYLPHENYLPHOSPHINOTHIOIC ACID - A NEW NMR SOLVATING AGENT FOR DETERMINATION OF ENANTIOMERIC EXCESSES OF SULFOXIDES
    DRABOWICZ, J
    DUDZINSKI, B
    MIKOLAJCZYK, M
    [J]. TETRAHEDRON-ASYMMETRY, 1992, 3 (10) : 1231 - 1234
  • [8] ENANTIOSELECTIVE MICROBIAL REDUCTION OF TRANSITION-METAL-COMPLEXED AROMATIC KETONES
    GILLOIS, J
    BUISSON, D
    AZERAD, R
    JAOUEN, G
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (18) : 1224 - 1225
  • [9] DIASTEREOTOPIC GROUP-SELECTIVE REACTIONS AT PI-ARENE CHROMIUM DERIVATIVES - DEPROTONATION AND NUCLEOPHILIC-ADDITION REACTIONS OF SUBSTRATES BEARING BENZYLIC CHIRAL CENTERS
    HEPPERT, JA
    AUBE, J
    THOMASMILLER, ME
    MILLIGAN, ML
    TAKUSAGAWA, F
    [J]. ORGANOMETALLICS, 1990, 9 (03) : 727 - 739
  • [10] RACEMIZATION AND CLEAVAGE OF SULFOXIDES BY METHYLLITHIUM
    JACOBUS, J
    MISLOW, K
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (20) : 5228 - &