STEREOSELECTIVE SYNTHESIS OF HOMOCHIRAL ALPHA SUBSTITUTED ORTHO-METHOXYBENZYL ALCOHOLS VIA NUCLEOPHILIC ADDITIONS TO KINETICALLY RESOLVED HOMOCHIRAL TRICARBONYL (ETA-6-ORTHO-ANISALDEHYDE)CHROMIUM(0)

被引:93
作者
BROMLEY, LA [1 ]
DAVIES, SG [1 ]
GOODFELLOW, CL [1 ]
机构
[1] DYSON PERRINS LAB,S PARKS RD,OXFORD OX1 3QY,ENGLAND
关键词
D O I
10.1016/S0957-4166(00)80533-9
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Tricarbonyl(eta-6-omicron-anisaldehyde)chromium(0) has been kinetically resolved via the selective hydrolysis of one of the L-valinol derived imine diastereoisomers in the presence of deactivated alumina. An X-ray crystal structure analysis on the adduct formed between L-valinol and homochiral (+)-tricarbonyl (eta-6-omicron-anisaldehyde)chromium(0) unambiguously established the presence of the corresponding imine and not oxazolidine and confirmed the absolute configuration of the aldehyde complex. Addition of Grignard reagents to homochiral tricarbonyl(eta-6-omicron-anisaldehyde)chromium(0) occurs completely stereoselectively to give, following decomplexation, homochiral alpha substituted omicron-methoxybenzyl alcohols.
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页码:139 / 156
页数:18
相关论文
共 40 条
  • [1] ABDALLAH H, 1982, TETRAHEDRON LETT, V23, P503
  • [2] AZOLE CHEMISTRY .7. EFFECT OF METAL COMPLEXATION ON A RING-CHAIN TAUTOMERIC EQUILIBRIUM
    ALPER, H
    DINKES, LS
    LENNON, PJ
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1973, 57 (01) : C12 - C14
  • [3] [Anonymous], 1974, INT TABLES XRAY CRYS, VIV, p[99, 149]
  • [4] ASYMMETRIC DARZENS CONDENSATION ON CHIRAL ETA-6CR(CO)3 COMPLEXED BENZALDEHYDES
    BALDOLI, C
    DELBUTTERO, P
    MAIORANA, S
    [J]. TETRAHEDRON, 1990, 46 (23) : 7823 - 7830
  • [5] NOREPHEDRINE-DERIVED 2-ALKENYLOXAZOLIDINES - STEREOCHEMISTRY OF CYCLIZATION AND ALLYLIC STEREOCENTER DIRECTED ASYMMETRIC CONJUGATE ADDITION
    BERNARDI, A
    CARDANI, S
    PILATI, T
    POLI, G
    SCOLASTICO, C
    VILLA, R
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (08) : 1600 - 1607
  • [6] BESANCON J, 1971, B SOC CHIM FR, P1804
  • [7] DIASTEREOSPECIFIC REFORMATSKY REACTION ON A CHIRAL TRICARBONYLCHROMIUM BENZALDEHYDE
    BROCARD, J
    PELINSKI, L
    LEBIBI, J
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1987, 336 (03) : C47 - C49
  • [8] DIASTEREOSELECTIVE KETOLIZATION OF CHIRAL BENZALDEHYDE TRICARBONYL CHROMIUM
    BROCARD, J
    MAHMOUDI, M
    PELINSKI, L
    MACIEJEWSKI, L
    [J]. TETRAHEDRON, 1990, 46 (20) : 6995 - 7002
  • [9] WEIGHTING SCHEME FOR LEAST-SQUARES STRUCTURE REFINEMENT
    CARRUTHERS, JR
    WATKIN, DJ
    [J]. ACTA CRYSTALLOGRAPHICA SECTION A, 1979, 35 (JUL): : 698 - 699
  • [10] CARRUTHERS JR, 1984, CRYSTALS USER MANUAL