Stereoselective synthesis and use in catalytic asymmetric addition of diethylzinc to benzaldehyde of new chiral amino alcohol complexes: Influence of the chromium complexation on the enantioselectivity

被引:26
作者
Malfait, S [1 ]
Pelinski, L [1 ]
Brocard, J [1 ]
机构
[1] UNIV LILLE 1,CATALYSE HETEROGENE & HOMOGENE LAB,GRP SYNTH ORGANOMET,URA CNRS 402,F-59655 VILLENEUVE DASCQ,FRANCE
关键词
D O I
10.1016/0957-4166(96)00056-0
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The optically active amino alcohol (arene)chromium (+)-(S,1S)-3-6 complexes were synthesized from enantiomerically pure indanone complex. As well as their uncomplexed counterparts, they have been used as chiral catalysts in the asymmetric addition of diethylzinc to benzaldehyde: 1-Phenylpropanol has obtained in up to 70% enantiomeric excess. A beneficial effect of the tricarbonyl chromium tripod on the enantioselectivity has been shown. (C) 1996 Elsevier Science Ltd
引用
收藏
页码:653 / 656
页数:4
相关论文
共 22 条
[1]   CATALYTIC ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES - SYNTHESIS AND APPLICATION OF A NEW CYCLIC CATALYST [J].
BEHNEN, W ;
MEHLER, T ;
MARTENS, J .
TETRAHEDRON-ASYMMETRY, 1993, 4 (07) :1413-1416
[2]   OPTICALLY-ACTIVE BIPYRIDINES IN ASYMMETRIC CATALYSIS [J].
BOLM, C ;
ZEHNDER, M ;
BUR, D .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (02) :205-207
[3]   SUCCESSIVE REGIOSPECIFIC AND STEREOSPECIFIC FUNCTIONALIZATION OF ETA(6)-ARENETRICARBONYLCHROMIUM IN POSITIONS META AND ORTHO [J].
BROCARD, J ;
GOETGHELUCK, S ;
PELINSKI, L .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1994, 476 (01) :C12-C14
[4]   HIGHLY REGIO-CONTROLLED AND STEREO-CONTROLLED HYDROFORMYLATION OF ORTHO-SUBSTITUTED (ETA(6)-STYRENE) CHROMIUM COMPLEXES [J].
BROCARD, J ;
PELINSKI, L ;
MACIEJEWSKI, L ;
NAILI, S ;
BRICOUT, H ;
MORTREUX, A ;
PETIT, F .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1994, 483 (1-2) :C1-C5
[5]  
GRACEY DEF, 1965, J CHEM SOC CHEM COMM, P566
[6]  
INLIANO A, 1995, TETRAHEDRON-ASYMMETR, V3, P739
[7]   SOME FACILE SYNTHESES OF OPTICALLY-ACTIVE 2-SUBSTITUTED INDANONES, INDANOLS, TETRALONES, AND TETRALOLS VIA THEIR CHROMIUM TRICARBONYL COMPLEXES [J].
JAOUEN, G ;
MEYER, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (16) :4667-4672
[8]   CATALYTIC ASYMMETRIC INDUCTION .2. CHIRAL TRICARBONYL (ETA-6 ARENE) CHROMIUM (0) COMPLEXES AS ENANTIOSELECTIVE CATALYSTS [J].
JONES, GB ;
HEATON, SB .
TETRAHEDRON-ASYMMETRY, 1993, 4 (02) :261-272
[9]   ENANTIOPURE 1-HYDROXYMETHYL-2-DIMETHYLAMINOMETHYLFERROCENE AS EFFICIENT CATALYST IN THE ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES [J].
NICOLOSI, G ;
PATTI, A ;
MORRONE, R ;
PIATTELLI, M .
TETRAHEDRON-ASYMMETRY, 1994, 5 (09) :1639-1642
[10]  
Noyori R., 1994, ASYMMETRIC CATALYSIS, P255