Novel enantiocomplementary C2-Symmetric chiral bis(imidazoline) ligands:: Highly enantioselective Friedel-Crafts alkylation of Indoles with ethyl 3,3,3-trifluoropyruvate

被引:111
作者
Nakamura, Shuichi [1 ]
Hyodo, Kengo [1 ]
Nakamura, Yuko [1 ]
Shibata, Norio [1 ]
Toru, Takeshi [1 ]
机构
[1] Nagoya Inst Technol, Dept Appl Chem, Grad Sch Engn, Showa Ku, Nagoya, Aichi 4668555, Japan
关键词
asymmetric catalysis; Friedel-Crafts reaction; imidazolines; Lewis acids;
D O I
10.1002/adsc.200800189
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Enantioselective Friedel-Crafts alkylations of a variety of indoles with ethyl 3,3,3-trifluoropyruvate catalyzed by novel chiral m-phenylenebis(imidazoline)-copper(II) complexes or the bis(imidazoline)-achiral acid combination afforded products with high enantioselectivity. Both enantiomers of indole derivatives can be prepared with high enantioselectivities by tuning the N-substituents of the imidazoline.
引用
收藏
页码:1443 / 1448
页数:6
相关论文
共 77 条
[1]   Synthesis of C2-Symmetric bisamidines:: A new type of chiral metal-free lewis acid analogue interacting with carbonyl groups [J].
Akalay, Deniz ;
Duerner, Gerd ;
Bats, Jan W. ;
Bolte, Michael ;
Goebel, Michael W. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (15) :5618-5624
[2]   Synthesis of a novel class of chiral N,N,N-tridentate pyridinebisimidazoline ligands and their application in Ru-catalyzed asymmetric epoxidations [J].
Anilkumar, G ;
Bhor, S ;
Tse, MK ;
Klawonn, M ;
Bitterlich, B ;
Beller, M .
TETRAHEDRON-ASYMMETRY, 2005, 16 (21) :3536-3561
[3]   Design and synthesis of a chiral N-tethered bis(imidazoline) ligand [J].
Arai, T ;
Mizukami, T ;
Yokoyama, N ;
Nakazato, D ;
Yanagisawa, A .
SYNLETT, 2005, (17) :2670-2672
[4]   Reaction optimization using solid-phase catalysis-CD HTS:: Nb-imidazoline-Cu(I)-catalyzed asymmetric benzoylation of 1,2-diols [J].
Arai, Takayoshi ;
Mizukami, Tomoe ;
Yanagisawa, Akira .
ORGANIC LETTERS, 2007, 9 (06) :1145-1147
[5]   New catalytic approaches in the stereoselective Friedel-Crafts alkylation reaction [J].
Bandini, M ;
Melloni, A ;
Umani-Ronchi, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (05) :550-556
[6]  
Bandini M., 2004, ANGEW CHEM, V116, P560
[7]   Organocatalytic asymmetric Friedel-Crafts alkylation of indoles with simple α,β-unsaturated ketones [J].
Bartoli, Giuseppe ;
Bosco, Marcella ;
Carlone, Armando ;
Pesciaioli, Fabio ;
Sambri, Letizia ;
Melchiorre, Paolo .
ORGANIC LETTERS, 2007, 9 (07) :1403-1405
[8]   Insights into CO/styrene copolymerization by using PdII catalysts containing modular pyridine-imidazoline ligands [J].
Bastero, A ;
Claver, C ;
Ruiz, A ;
Castillón, S ;
Daura, E ;
Bo, C ;
Zangrando, E .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (15) :3747-3760
[9]   Influence of pyridine-imidazoline ligands on the reactivity of palladium-methyl complexes with carbon monoxide [J].
Bastero, A ;
Ruiz, A ;
Claver, C ;
Milani, B ;
Zangrando, E .
ORGANOMETALLICS, 2002, 21 (26) :5820-5829
[10]  
Bastero A, 2001, EUR J INORG CHEM, P3009