Enantioselective addition of dialkylzinc to aldehydes catalyzed by (S)-2-(N,N-disubstituted aminomethyl)indoline

被引:55
作者
Asami, M [1 ]
Watanabe, H [1 ]
Honda, K [1 ]
Inoue, S [1 ]
机构
[1] Yokohama Natl Univ, Fac Engn, Dept Synthet Chem, Hodogaya Ku, Yokohama, Kanagawa 2408501, Japan
关键词
D O I
10.1016/S0957-4166(98)00446-7
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Chiral di- or triamines, (S)-2-(N,N-disubstituted aminomethyl)indoline 1a-d, derived from (S)-indoline-2-carboxylic acid were efficient chiral catalysts for the enantioselective addition of dialkylzincs to aldehydes. The best results were obtained by employing 15 mol% of (S)-2-(4-methylpiperazin-1-ylmethyl)indoline Ic, and chiral secondary alcohols were obtained in up to 97% ee. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4165 / 4173
页数:9
相关论文
共 25 条
[1]   Enantioselective addition of diethylzinc to aldehydes catalyzed by (S)-2-(N,N-disubstituted aminomethyl)pyrrolidine [J].
Asami, M ;
Inoue, S .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1997, 70 (07) :1687-1690
[2]   Functionalized 2-azabicyclo[3.3.0]octanes as ligands in the enantioselective catalysis [J].
Aurich, HG ;
Soeberdt, M .
TETRAHEDRON LETTERS, 1998, 39 (17) :2553-2554
[3]   Novel ligands derived from S-tyrosine for the enantioselective addition of diethylzinc to aldehydes [J].
Beliczey, J ;
Giffels, G ;
Kragl, U ;
Wandrey, C .
TETRAHEDRON-ASYMMETRY, 1997, 8 (10) :1529-1530
[4]   CATALYZED ENANTIOSELECTIVE ALKYLATION OF ALDEHYDES [J].
BOLM, C ;
SCHLINGLOFF, G ;
HARMS, K .
CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (05) :1191-1203
[5]   CHIRAL LIGANDS CONTAINING HETEROATOMS .8. 2-[(2S)-2-PYRROLIDINYL]PYRIDINE AS A NOVEL CATALYST IN THE ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES [J].
CHELUCCI, G ;
CONTI, S ;
FALORNI, M ;
GIACOMELLI, G .
TETRAHEDRON, 1991, 47 (38) :8251-8258
[6]   Enantioselective addition of diethylzinc to aldehydes catalyzed by a new chiral β-amino alcohol derived from D-mannitol [J].
Cho, BT ;
Chun, YS .
TETRAHEDRON-ASYMMETRY, 1998, 9 (09) :1489-1492
[7]   Chiral ligands derived from Abrine .2. Oxazolidines as promoters for enantioselective addition of diethylzinc toward aromatic aldehydes [J].
Dai, WM ;
Zhu, HJ ;
Hao, XJ .
TETRAHEDRON-ASYMMETRY, 1996, 7 (05) :1245-1248
[8]   Syntheses of new chiral 1,2-diamines and delta-amino-alcohols and their application in catalytic enantioselective C-C bond formations at an elevated temperature of up to 110 degrees C [J].
Eilers, J ;
Wilken, J ;
Martens, J .
TETRAHEDRON-ASYMMETRY, 1996, 7 (08) :2343-2357
[9]   THIOL AND DISULFIDE DERIVATIVES OF EPHEDRA ALKALOIDS .2. A MECHANISTIC STUDY OF THEIR EFFECT ON THE ADDITION OF DIETHYL ZINC TO BENZALDEHYDE [J].
FITZPATRICK, K ;
HULST, R ;
KELLOGG, RM .
TETRAHEDRON-ASYMMETRY, 1995, 6 (08) :1861-1864