Enantioselective addition of diethylzinc to benzaldehyde catalyzed by ferrocenic amino-alcohols combining centered and planar chiralities

被引:13
作者
Malézieux, B
Andrés, R
Gruselle, M
Rager, MN
Thorimbert, S
机构
[1] Univ Paris 06, CNRS, Unite 7071, Lab Chim Inorgan & Mat Mol, F-75252 Paris 05, France
[2] Ecole Natl Super Chim Paris, Serv RMN, F-75231 Paris, France
[3] Univ Paris 06, UMR 7611, Lab Chim Organ Synth, F-75252 Paris 05, France
关键词
D O I
10.1016/S0957-4166(99)00307-9
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Diastereomeric ferrocenic amino-alcohols combining three elements of chirality (one of which is a ferrocenic plane) are tested as catalysts in the alkylation of benzaldehyde with diethylzinc. Good to excellent yields and ees were obtained and show correlation between the metallocenic chirality and the configuration of the resulting 1-phenyl-1-propanol. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3253 / 3257
页数:5
相关论文
共 20 条
[1]   On the role of planar chirality in asymmetric catalysis:: A study toward appropriate ferrocene ligands for diethylzinc additions [J].
Bolm, C ;
Muñiz-Fernández, K ;
Seger, A ;
Raabe, G ;
Günther, K .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) :7860-7867
[2]   Planar-chiral heterocycles as ligands in metal-catalyzed processes: Enantioselective addition of organozinc reagents to aldehydes [J].
Dosa, PI ;
Ruble, JC ;
Fu, GC .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (03) :444-445
[3]   DIASTEREOSELECTIVE SYNTHESIS OF 3-(2-((N,N-DIMETHYLAMINO)METHYL)FERROCENYL)-4-(4-METHOXYPHENYL)HEXAN-3-OLS, IN RACEMIC AND OPTICALLY-ACTIVE SERIES - X-RAY DETERMINATION OF THEIR RELATIVE CONFIGURATION [J].
GRUSELLE, M ;
MALEZIEUX, B ;
TROITSKAYA, LL ;
SOKOLOV, VI ;
EPSTEIN, LM ;
SHUBINA, YS ;
VAISSERMANN, J .
ORGANOMETALLICS, 1994, 13 (01) :200-207
[4]   CATALYTIC ASYMMETRIC INDUCTION - HIGHLY ENANTIOSELECTIVE ADDITION OF DIALKYLZINCS TO ALDEHYDES [J].
KITAMURA, M ;
SUGA, S ;
KAWAI, K ;
NOYORI, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (19) :6071-6072
[5]   Enantiospecific synthesis of 4-(4′-methoxyphenyl)-hexan-3-one as precursor for optically active (pS) or (pR) isomer of (Z) or (E)-3-(2′-((N,N-dimethylamino)methylferrocenyl)-4-(4"-methoxyphenyl)-hex-3-ene [J].
Malézieux, B ;
Gruselle, M ;
Troitskaya, L ;
Sokolov, V .
TETRAHEDRON-ASYMMETRY, 1998, 9 (02) :259-269
[6]   Enantioselective synthesis and use in catalytic asymmetric addition of diethylzinc to benzaldehyde of new chiral cyclic hydroxyamino ferrocene and chromium complexes:: influence of the complexation on the enantioselectivity [J].
Malfait, S ;
Pélinski, L ;
Brocard, J .
TETRAHEDRON-ASYMMETRY, 1998, 9 (15) :2595-2610
[7]   STEREOSELECTIVE SYNTHESES .5. CORRELATION OF CENTRAL AND PLANAR CHIRALITY IN FERROCENE DERIVATIVES [J].
MARQUARDING, D ;
KLUSACEK, H ;
GOKEL, G ;
HOFFMANN, P ;
UGI, I .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (18) :5389-+
[8]  
MORI A, 1992, SYNLETT, P427
[9]  
MUCHOW G, 1987, TETRAHEDRON LETT, V28, P6163
[10]   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