Enantioselective synthesis of quaternary α-aminophosphonates by organocatalytic Friedel-Crafts reactions of indoles with cyclic α-ketiminophosphonates

被引：16
|
作者：
Yan, Zhong [1 ]
Gao, Xiang [1 ]
Zhou, Yong-Gui [1 ]
机构：
[1] Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Liaoning, Peoples R China
来源：
CHINESE JOURNAL OF CATALYSIS | 2017年 / 38卷 / 05期
基金：
中国国家自然科学基金;
关键词：
Friedel-Crafts reaction; Quaternary alpha-aminophosphonate; Indole; Chiral phosphoric acid; CHIRAL PHOSPHORIC-ACID; C BOND FORMATION; ASYMMETRIC-SYNTHESIS; BRONSTED ACID; STEREOSELECTIVE-SYNTHESIS; ALKYLATION REACTION; DERIVATIVES; AMINO; CONSTRUCTION; IMINES;
D O I：
10.1016/S1872-2067(17)62804-3
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
An efficient asymmetric Friedel-Crafts reaction has been developed for the synthesis of optically active quaternary alpha-aminophosphonates with up to 98% ee. The synthesis involves the reaction of cyclic alpha-ketiminophosphonates with indoles using an H8-BINOL-derived chiral phosphoric acid (CPA) catalyst that bears electron-withdrawing 3,5-ditrifluoromethylphenyl substituents on its 3- and 3'-positions. This Friedel-Crafts reaction of cyclic alpha-ketiminophosphonates was also successful with pyrrole. (C) 2017, Dalian Institute of Chemical Physics, Chinese Academy of Sciences. Published by Elsevier B.V. All rights reserved.
引用
收藏
页码：784 / 792
页数：9
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