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
相关论文
共 51 条
[1]   PHOSPHONOPEPTIDES, A NEW CLASS OF SYNTHETIC ANTIBACTERIAL AGENTS [J].
ALLEN, JG ;
ATHERTON, FR ;
HALL, MJ ;
HASSALL, CH ;
HOLMES, SW ;
LAMBERT, RW ;
NISBET, LJ ;
RINGROSE, PS .
NATURE, 1978, 272 (5648) :56-58
[2]  
Christoffers J, 2001, ANGEW CHEM INT EDIT, V40, P4591, DOI 10.1002/1521-3773(20011217)40:24<4591::AID-ANIE4591>3.0.CO
[3]  
2-V
[4]   Asymmetric Bronsted acid catalyzed isoindoline synthesis: Enhancement of enantiomeric ratio by stereoablative kinetic resolution [J].
Enders, Dieter ;
Narine, Arun A. ;
Toulgoat, Fabien ;
Bisschops, Tom .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (30) :5661-5665
[5]   The highly enantioselective addition of indoles and pyrroles to isatins-derived N-Boc ketimines catalyzed by chiral phosphoric acids [J].
Feng, Jingchao ;
Yan, Wenjin ;
Wang, Dong ;
Li, Peng ;
Sun, Quantao ;
Wang, Rui .
CHEMICAL COMMUNICATIONS, 2012, 48 (64) :8003-8005
[6]  
Huang JM, 2000, HETEROATOM CHEM, V11, P480, DOI 10.1002/1098-1071(2000)11:7<480::AID-HC6>3.0.CO
[7]  
2-J
[8]   Enantioselective Organocatalytic Synthesis of Quaternary α-Amino Acids Bearing a CF3 Moiety [J].
Husmann, Ralph ;
Sugiono, Erli ;
Mersmann, Stefanie ;
Raabe, Gerhard ;
Rueping, Magnus ;
Bolm, Carsten .
ORGANIC LETTERS, 2011, 13 (05) :1044-1047
[9]   Chiral bronsted acid catalyzed enantioselective Friedel-Crafts reaction of indoles and α-aryl enamides:: Construction of quaternary carbon atoms [J].
Jia, Yi-Xia ;
Zhong, Jun ;
Zhu, Shou-Fei ;
Zhang, Can-Ming ;
Zhou, Qi-Lin .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (29) :5565-5567
[10]   Asymmetric Friedel-Crafts addition of indoles to N-sulfonyl aldimines:: A simple approach to optically active 3-indolyl-methanamine derivatives [J].
Jia, YX ;
Xie, JH ;
Duan, HF ;
Wang, LX ;
Zhou, QL .
ORGANIC LETTERS, 2006, 8 (08) :1621-1624
123456