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

来源：

TETRAHEDRON-ASYMMETRY | 1991年 / 2卷 / 02期

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.

引用

页码：139 / 156

页数：18

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

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