Synthesis of new chiral catalysts, pyridyl- and bipyridylalcohols, for the enantioselective addition of diethylzinc to benzaldehyde

被引:43
作者
Collomb, P
von Zelewsky, A
机构
[1] Novartis Nutr Res, CH-3176 Neuenegg, Switzerland
[2] Univ Fribourg, Inst Inorgan & Analyt Chem, CH-1700 Fribourg, Switzerland
关键词
D O I
10.1016/S0957-4166(98)00399-1
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
New chiral ligands, pyridyl- and bipyridylalcohols, were prepared and their catalytic role in the reaction of diethylzinc with benzaldehyde to give 1-phenyl-1-propanol was studied. In several cases, the yields approach 100%, and ee-values of up to 86% are observed. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3911 / 3917
页数:7
相关论文
共 13 条
[1]  
[Anonymous], ANGEW CHEM
[2]   CATALYZED ENANTIOSELECTIVE ALKYLATION OF ALDEHYDES [J].
BOLM, C ;
SCHLINGLOFF, G ;
HARMS, K .
CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (05) :1191-1203
[3]  
Bolm C., 1990, Angew. Chem, V102, P206
[4]   DIASTEREOISOMERIC PURE 2-(1-HYDROXYALKYL)PYRIDINES AS CATALYSTS IN THE ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES [J].
CHELUCCI, G ;
SOCCOLINI, F .
TETRAHEDRON-ASYMMETRY, 1992, 3 (10) :1235-1238
[5]   CHIRAL LIGANDS CONTAINING HETEROATOMS .6. 1-(2-PYRIDYLMETHYL)PYRROLIDINE IN THE CHIRAL CATALYSIS OF ADDITION OF DIETHYLZINC TO BENZALDEHYDE [J].
CHELUCCI, G ;
FALORNI, M ;
GIACOMELLI, G .
TETRAHEDRON-ASYMMETRY, 1990, 1 (11) :843-849
[6]   Synthesis of new chiral catalysts, substituted 2-phenyl-5,6,7,8-tetrahydro-6,6-dimethyl-5,7-methano-quinolines, for the enantioselective addition of diethylzinc to benzaldehyde [J].
Collomb, P ;
vonZelewsky, A .
TETRAHEDRON-ASYMMETRY, 1995, 6 (12) :2903-2904
[7]   NEW VERSATILE OPTICALLY-ACTIVE BIPYRIDINES AS BUILDING-BLOCKS FOR HELICATING AND CAGING LIGANDS [J].
HAYOZ, P ;
VONZELEWSKY, A .
TETRAHEDRON LETTERS, 1992, 33 (36) :5165-5168
[8]   CATALYZED ASYMMETRIC REACTION OF ALDEHYDES WITH DIALKYLZINC IN THE PRESENCE OF CHIRAL PYRIDYL ALCOHOLS AS LIGANDS [J].
ISHIZAKI, M ;
FUJITA, K ;
SHIMAMOTO, M ;
HOSHINO, O .
TETRAHEDRON-ASYMMETRY, 1994, 5 (03) :411-424
[9]   ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES CATALYZED BY PYRIDINEOXAZOLINEALCOHOLS [J].
MACEDO, E ;
MOBERG, C .
TETRAHEDRON-ASYMMETRY, 1995, 6 (02) :549-558
[10]   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 [J].
Malfait, S ;
Pelinski, L ;
Brocard, J .
TETRAHEDRON-ASYMMETRY, 1996, 7 (03) :653-656