Chiroptical properties and applications in PTC of new dendritic cinchonidine-derived ammonium salts

被引:29
作者
Guillena, G
Kreiter, R
van de Coevering, R
Gebbink, RJMK
van Koten, G
Mazón, P
Chinchilla, R
Nájera, C
机构
[1] Univ Utrecht, Debye Inst, Dept Met Mediated Synth, NL-3584 CH Utrecht, Netherlands
[2] Univ Alicante, Fac Ciencias, Dept Quim Organ, E-03080 Alicante, Spain
关键词
D O I
10.1016/j.tetasy.2003.08.030
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Chiral nanosize molecules, derived from cinchonidine and Frechet dendritic wedges up to generation three, have been synthesized. The chiroptical properties, optical rotation and circular dichroism of these systems have been studied. These chiral dendritic molecules have been used as phase transfer catalysts in the alkylation of a glycine imine ester, showing a promising level of asymmetric induction. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3705 / 3712
页数:8
相关论文
共 57 条
[41]  
2-3
[42]   Chirality in dendritic architectures [J].
Peerlings, HWI ;
Meijer, EW .
CHEMISTRY-A EUROPEAN JOURNAL, 1997, 3 (10) :1563-1570
[43]  
Rheiner PB, 1999, CHEM-EUR J, V5, P3221, DOI 10.1002/(SICI)1521-3765(19991105)5:11<3221::AID-CHEM3221>3.0.CO
[44]  
2-P
[45]   Chiral dendrimers - from architecturally interesting hyperbranched macromolecules to functional materials [J].
Romagnoli, B ;
Hayes, W .
JOURNAL OF MATERIALS CHEMISTRY, 2002, 12 (04) :767-799
[46]  
Sanders-Hovens M. S. T. H., 1995, POLYM MAT SCI ENG, V73, P338
[47]   Highly enantioselective addition of dialkylzincs to aldehydes using dendritic chiral catalysts with flexible carbosilane backbones [J].
Sato, I ;
Kodaka, R ;
Hosoi, K ;
Soai, K .
TETRAHEDRON-ASYMMETRY, 2002, 13 (08) :805-808
[48]   Synthesis of chiral dendrimers with a hydrocarbon backbone and application to the catalytic enantioselective addition of dialkylzincs to aldehydes [J].
Sato, I ;
Shibata, T ;
Ohtake, K ;
Kodaka, R ;
Hirokawa, Y ;
Shirai, N ;
Soai, K .
TETRAHEDRON LETTERS, 2000, 41 (17) :3123-3126
[49]   First example of high asymmetric induction at the "pseudo-micellar" interface of a chiral amphiphilic dendrimer [J].
Schmitzer, A ;
Perez, E ;
Rico-Lattes, I ;
Lattes, A .
TETRAHEDRON LETTERS, 1999, 40 (15) :2947-2950
[50]  
Seebach D, 1998, TOP CURR CHEM, V197, P125