Enantioselective Synthesis of Unsymmetrical Triarylmethanes by Chiral Bronsted Acids

被引：154

作者：

Sun, Feng-Lai ^{[1
]}

Zheng, Xiao-Jian ^{[1
]}

Gu, Qing ^{[1
]}

He, Qing-Li ^{[1
]}

You, Shu-Li ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 01期

基金：

中国国家自然科学基金;

关键词：

Chiral Bronsted acids; Enantioselectivity; Friedel-Crafts reaction; Indole; Organocatalysis; FRIEDEL-CRAFTS REACTION; ELECTRON-RICH ARENES; ARYLBORONIC ACIDS; PHOSPHORIC-ACIDS; ALKYLATION; INDOLES; IMINES; DERIVATIVES; CATALYST; ACCESS;

D O I：

10.1002/ejoc.200901164

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral Bronsted acid catalyzed Friedel-Crafts alkylation of electron-rich arenes with (3-indolyl)methanamines has been realized to provide an efficient synthesis of enantioenriched unsymmetrical triarylmethanes. With 5 mol-% of a newly developed chiral phosphoric acid, the enantioenriched unsymmetrical triarylmethanes were obtained in excellent yields with up to 91 % ee.

引用

页码：47 / 50

页数：4

共 50 条

[1] Enantioselective Transformations Catalyzed by Chiral Bronsted Acids [J].

Terada, Masahiro .

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2013, 71 (05) :480-490

[2] Chiral Bronsted acid-catalyzed conjugate addition of indoles to azadienes: Enantioselective synthesis of hetero-triarylmethanes [J].

Xie, Huan-Ping ;

Wu, Bo ;

Wang, Xin-Wei ;

Zhou, Yong-Gui .

CHINESE JOURNAL OF CATALYSIS, 2019, 40 (10) :1566-1575

[3] Enantioselective Synthesis of Triarylmethanes by Chiral Imidodiphosphoric Acids Catalyzed Friedel-Crafts Reactions [J].

Zhuo, Ming-Hua ;

Jiang, Yi-Jun ;

Fan, Yan-Sen ;

Gao, Yang ;

Liu, Song ;

Zhang, Suoqin .

ORGANIC LETTERS, 2014, 16 (04) :1096-1099

[4] Bronsted Acidic Ionic Liquid Catalyzed Three-Component Friedel-Crafts Reaction for the Synthesis of Unsymmetrical Triarylmethanes [J].

Rinkam, Suttida ;

Senapak, Warapong ;

Watchasit, Sarayut ;

Saeeng, Rungnapha ;

Sirion, Uthaiwan .

SYNLETT, 2022, 33 (14) :1383-1390

[5] Highly Enantioselective Friedel-Crafts Reaction of 4,7-Dihydroindoles with β,γ-Unsaturated α-Keto Esters by Chiral Bronsted Acids [J].

Zeng, Mi ;

Kang, Qiang ;

He, Qing-Li ;

You, Shu-Li .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (14-15) :2169-2173

[6] Enantioselective Addition Reaction of Azlactones with Styrene Derivatives Catalyzed by Strong Chiral BrOnsted Acids [J].

Kikuchi, Jun ;

Terada, Masahiro .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (25) :8458-8462

[7] Chiral Bronsted-Acid-Catalyzed Enantioselective Arylation of Ethyl Trifluoroacetoacetate and Ethyl Trifluoropyruvate [J].

Nie, Jing ;

Zhang, Guang-Wu ;

Wang, Lian ;

Zheng, Dong-Hua ;

Zheng, Yan ;

Ma, Jun-An .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (19) :3145-3149

[8] Bronsted Acid Catalyzed Synthesis of Unsymmetrical Arylbis(3-indolyl)methanes [J].

He, Qing-Li ;

Sun, Feng-Lai ;

Zheng, Xiao-Jian ;

You, Shu-Li .

SYNLETT, 2009, (07) :1111-1114

[9] Asymmetric Friedel-Crafts Reaction of 4,7-Dihydroindoles with Nitroolefins by Chiral Bronsted Acids under Low Catalyst Loading [J].

Sheng, Yi-Fei ;

Li, Gong-Qiang ;

Kang, Qiang ;

Zhang, An-Jiang ;

You, Shu-Li .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (14) :3351-3354

[10] Enantioselective N-H Functionalization of Indoles with α,β-Unsaturated γ-Lactams Catalyzed by Chiral Bronsted Acids [J].

Xie, Yinjun ;

Zhao, Yingwei ;

Qian, Bo ;

Yang, Lei ;

Xia, Chungu ;

Huang, Hanmin .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (25) :5681-5685

← 1 2 3 4 5 →