A NEW ASYMMETRIC-SYNTHESIS OF TRICARBONYLCHROMIUM COMPLEXES OF ORTHO-SUBSTITUTED BENZALDEHYDES

被引:40
作者
KUNDIG, EP
LIU, RG
RIPA, A
机构
[1] Départment de Chimie Organique, Université de Genève, Genève, CH-1211, 30, quai Ernest-Ansermet
关键词
D O I
10.1002/hlca.19920750818
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
ortho-Substituted [Cr(CO)3(benzaldehyde)) complexes are obtained via nucleophilic addition of alkyl- and aryllithium reagents to a [Cr(CO)3(phenylmethaneimine)] complex followed by endo-hydride abstraction with triphenylmethyl cation. This sequence, when carried out with a [Cr(CO)3(benzaldehyde SAMP hydrazone)] complex affords substituted derivatives (Me, Bu, Ph, vinyl) with high ( greater-than-or-equal-to 97 %) diastereoselectivity and, after hydrolysis, ortho-substituted [Cr(CO)3(benzaldehyde)] ((S)-1) complexes of high enantiomeric purity.
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收藏
页码:2657 / 2660
页数:4
相关论文
共 39 条
[1]   RESOLUTION AND ASYMMETRIC-SYNTHESIS OF ORTHO-SUBSTITUTED (BENZALDEHYDE)TRICARBONYLCHROMIUM COMPLEXES [J].
ALEXAKIS, A ;
MANGENEY, P ;
MAREK, I ;
ROSEMUNCH, F ;
ROSE, E ;
SEMRA, A ;
ROBERT, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (21) :8288-8290
[2]   ASYMMETRIC DEPROTONATION AND COMPLEXATION REACTIONS MEDIATED BY CHIRAL KETALS AS A ROUTE TO ORTHO-DISUBSTITUTED (ETA-6-ARENE)CR(CO)3 COMPLEXES [J].
AUBE, J ;
HEPPERT, JA ;
MILLIGAN, ML ;
SMITH, MJ ;
ZENK, P .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (13) :3563-3570
[3]   ASYMMETRIC DARZENS CONDENSATION ON CHIRAL ETA-6CR(CO)3 COMPLEXED BENZALDEHYDES [J].
BALDOLI, C ;
DELBUTTERO, P ;
MAIORANA, S .
TETRAHEDRON, 1990, 46 (23) :7823-7830
[4]   SEPARATION OF RACEMIC MIXTURES OF ORGANOMETALLIC COMPLEXES BY USING CHIRAL SOLID SUPPORTS [J].
BITTERWOLF, TE ;
HUBLER, TL ;
TODIME, R .
JOURNAL OF MACROMOLECULAR SCIENCE-CHEMISTRY, 1990, A27 (9-11) :1437-1446
[5]  
BOUTONNET JC, 1987, B SOC CHIM FR, P640
[6]   DIASTEREOSELECTIVE KETOLIZATION OF CHIRAL BENZALDEHYDE TRICARBONYL CHROMIUM [J].
BROCARD, J ;
MAHMOUDI, M ;
PELINSKI, L ;
MACIEJEWSKI, L .
TETRAHEDRON, 1990, 46 (20) :6995-7002
[7]  
BROCARD J, 1987, J ORGANOMET CHEM, V337, pC47
[8]   STEREOSELECTIVE SYNTHESIS OF HOMOCHIRAL ALPHA SUBSTITUTED ORTHO-METHOXYBENZYL ALCOHOLS VIA NUCLEOPHILIC ADDITIONS TO KINETICALLY RESOLVED HOMOCHIRAL TRICARBONYL (ETA-6-ORTHO-ANISALDEHYDE)CHROMIUM(0) [J].
BROMLEY, LA ;
DAVIES, SG ;
GOODFELLOW, CL .
TETRAHEDRON-ASYMMETRY, 1991, 2 (02) :139-156
[9]  
COLLMAN JP, 1987, PRINCIPLES APPL ORGA, P922
[10]   STEREOSELECTIVE SYNTHESIS OF BETA-HYDROXYAMINO ACIDS BY ALDOL REACTION OF ALPHA-ISOCYANOCARBOXYLATE WITH ARENE-CHROMIUM-TRICARBONYL COMPLEXES [J].
COLONNA, S ;
MANFREDI, A ;
SOLLADIECAVALLO, A ;
QUAZZOTTI, S .
TETRAHEDRON LETTERS, 1990, 31 (43) :6185-6188