Synthesis of C2-symmetrical 1,1′-disubstituted ferrocenyl amino alcohols and use in catalytic asymmetric addition of diethylzinc to benzaldehyde

被引:26
作者
Bastin, S
Delebecque, N
Agbossou, F
Brocard, J
Pélinski, L [1 ]
机构
[1] Ecole Natl Super Chim Lille, UPRESA 8010, Catalyse Lab, Grp Synthese Organomet, F-59655 Villeneuve Dascq, France
[2] Ecole Natl Super Chim Lille, UPRESA 8010, Catalyse Lab, Grp Chim Organ Appl, F-59655 Villeneuve Dascq, France
关键词
D O I
10.1016/S0957-4166(99)00181-0
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Optically active C-2-symmetrical 1,1'-disubstituted ferrocenyl amino alcohols have been used as chiral catalysts in the asymmetric addition of diethylzinc to benzaldehyde. 1-Phenylpropanol has been obtained in up to 83% enantiomeric excess. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1647 / 1651
页数:5
相关论文
共 24 条
[1]   ENANTIOSELECTIVE ETHYLATION OF ALDEHYDES CATALYZED BY CHIRAL C-2-SYMMETRICAL BETA-HYDROXY-M-XYLYLENE DIAMINES [J].
ANDRES, JM ;
MARTINEZ, MA ;
PEDROSA, R ;
PEREZENCABO, A .
TETRAHEDRON-ASYMMETRY, 1994, 5 (01) :67-72
[2]   Synthesis of new enantiopure gamma-aminoalcohols: Their use as catalysts in the alkylation of benzaldehyde by diethylzinc [J].
Cicchi, S ;
Crea, S ;
Goti, A ;
Brandi, A .
TETRAHEDRON-ASYMMETRY, 1997, 8 (02) :293-301
[3]   CHIRAL LIGANDS CONTAINING HETEROATOMS .10. 1-(2-PYRIDYL)ALKYLAMINES AS CHIRAL CATALYSTS IN THE ADDITION OF DIETHYLZINC TO ALDEHYDES - TEMPERATURE-DEPENDENCE ON THE ENANTIOSELECTIVITY [J].
CONTI, S ;
FALORNI, M ;
GIACOMELLI, G ;
SOCCOLINI, F .
TETRAHEDRON, 1992, 48 (41) :8993-9000
[4]   Enantioselective synthesis of (R)- and (S)-1-ferrocenylalkylamines. Reduction of enantiopure ferrocenylimines obtained from valinol and phenylglycinol [J].
Glorian, G ;
Maciejewski, L ;
Brocard, J ;
Agbossou, F .
TETRAHEDRON-ASYMMETRY, 1997, 8 (03) :355-358
[5]   Highly stereoselective alkylation through asymmetric intramolecular autoactivation; Synthesis and use of a new chiral ligand [J].
Maciejewski, LA ;
Goetgheluck, SJ ;
Delacroix, OA ;
Brocard, JS .
TETRAHEDRON-ASYMMETRY, 1996, 7 (06) :1573-1576
[6]   Highly chemo- and diastereoselective addition of diethylzinc through intramolecular autoactivation of enantiopure 2-acyl-1-formylferrocene:: application to the synthesis of optically pure 1,2-diacylferrocenes [J].
Malfait, S ;
Pélinski, L ;
Brocard, J .
TETRAHEDRON-ASYMMETRY, 1998, 9 (13) :2207-2210
[7]  
Mino T, 1998, SYNLETT, P965
[8]   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
[9]   ASYMMETRIC-SYNTHESIS USING CHIRAL PIPERAZINES .3. ENANTIOSELECTIVE ADDITION OF DIALKYLZINCS TO ARYL ALDEHYDES CATALYZED BY CHIRAL PIPERAZINES [J].
NIWA, S ;
SOAI, K .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (11) :2717-2720
[10]   ENANTIOSELECTIVE ADDITION OF ORGANOMETALLIC REAGENTS TO CARBONYL-COMPOUNDS - CHIRALITY TRANSFER, MULTIPLICATION, AND AMPLIFICATION [J].
NOYORI, R ;
KITAMURA, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1991, 30 (01) :49-69