Highly Enantioselective Friedel-Crafts Reaction of Indole with Alkylidenemalonates Catalyzed by Heteroarylidene Malonate-Derived Bis(oxazoline) Copper(II) Complexes

被引：36
|
作者：
Sun, Yan-Jin [1 ]
Li, Nan [1 ]
Zheng, Zhong-Bo [1 ]
Liu, Lei [1 ]
Yu, Yan-Bo [1 ]
Qin, Zhao-Hai [1 ]
Fu, Bin [1 ]
机构：
[1] China Agr Univ, Dept Appl Chem, Beijing 100193, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2009年 / 351卷 / 18期
关键词：
asymmetric catalysis; bis(oxazolines); Friedel-Crafts reaction; heteroarylidenemalonates; indoles; ASYMMETRIC MICHAEL ADDITION; BIS(OXAZOLINYL)PYRIDINE-SCANDIUM(III) TRIFLATE COMPLEXES; DIELS-ALDER REACTIONS; LIGAND BITE-ANGLE; BENZYLIDENE MALONATE; 2-ACYL IMIDAZOLES; ARYLID-BOX; ALKYLATION; NITROALKENES; IMINES;
D O I：
10.1002/adsc.200900669
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A series of cheap and easily accessible heteroarylidenemalonate-derived bis(oxazoline) ligands 1 and 2 were synthesized and their copper(II) complexes were applied to the catalytic Friedel-Crafts reaction between indoles and diethyl alkylidenemalonates, Excellent asymmetric enantioselectivities were afforded for the S-enantiomer (up to > 99% ee) in isobutyl alcohol, and the R-enantiomer (up to 96.5% ee) in dichloromethane.
引用
收藏
页码：3113 / 3117
页数：5
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