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

页码：784 / 792

页数：9