Organocatalytic Enantioselective Synthesis of 6-Aryl-5,6-dihydrophenanthridines by a Modified Pictet-Spengler Reaction of Biphenyl-2-amines and Aromatic Aldehydes

被引：12

作者：

Wang, Chaoceng ^{[1
]}

An, Dong ^{[1
]}

Guan, Xukai ^{[1
]}

Fan, Yansen ^{[1
]}

Liu, Guofeng ^{[1
]}

Zhang, Guangliang ^{[1
]}

Zhang, Suoqin ^{[1
]}

机构：

[1] Jilin Univ, Coll Chem, Changchun 130012, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 14期

基金：

中国国家自然科学基金;

关键词：

Asymmetric synthesis; Enantioselectivity; Fusedring systems; Nitrogen heterocycles; Organocatalysis; AXIALLY CHIRAL BISPHOSPHORYLIMIDES; FRIEDEL-CRAFTS REACTIONS; BRONSTED ACIDS; BENZOPHENANTHRIDINE ALKALOIDS; CYCLIZATION REACTIONS; ZANTHOXYLUM-NITIDUM; DERIVATIVES; DIHYDROCHELERYTHRINE; ARYLATION; PATHWAY;

D O I：

10.1002/ejoc.201700185

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A straightforward approach to the enantioselective synthesis of chiral 5,6-dihydrophenanthridines was developed. A series of chiral 6-aryl-5,6-dihydrophenanthridines were obtained through an organocatalytically modified Pictet-Spengler reaction of biphenyl-2-amines and aromatic aldehydes. In the reaction, H-8-BINOL-derived chiral imidodiphosphoric acid exhibited strong stereocontrolling and catalytic activities to afford the desired 6-aryl-5,6-dihydrophenanthridines in high yields (up to 98 %) with high enantioselectivities (up to 99 % ee).

引用

页码：1865 / 1869

页数：5

共 57 条

[41] Potassium tert-Butoxide Promoted Intramolecular Arylation via a Radical Pathway [J].

Roman, Daniela Sustac ;

Takahashi, Yoko ;

Charette, Andre B. .

ORGANIC LETTERS, 2011, 13 (12) :3242-3245

[42] Catalytic asymmetric Pictet-Spengler reaction [J].

Seayad, J ;

Seayad, AM ;

List, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (04) :1086-1087

[43] The Pictet-Spengler Reaction in Nature and in Organic Chemistry [J].

Stoeckigt, Joachim ;

Antonchick, Andrey P. ;

Wu, Fangrui ;

Waldmann, Herbert .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (37) :8538-8564

[44] Neocuproine-KOtBu promoted intramolecular cross coupling to approach fused rings [J].

Sun, Chang-Liang ;

Gu, Yi-Fan ;

Huang, Wei-Ping ;

Shi, Zhang-Jie .

CHEMICAL COMMUNICATIONS, 2011, 47 (35) :9813-9815

[45] Highly enantioselective catalytic acyl-Pictet-Spengler reactions [J].

Taylor, MS ;

Jacobsen, EN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (34) :10558-10559

[46] C2-symmetric bicyclo[2.2.2]octadienes as chiral ligands:: Their high performance in rhodium-catalyzed asymmetric arylation of N-tosylarylimines [J].

Tokunaga, N ;

Otomaru, Y ;

Okamoto, K ;

Ueyama, K ;

Shintani, R ;

Hayashi, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (42) :13584-13585

[47] Wacker-Type Oxidation and Dehydrogenation of Terminal Olefins Using Molecular Oxygen as the Sole Oxidant without Adding Ligand [J].

Wang, Yu-Fei ;

Gao, Ya-Ru ;

Mao, Shuai ;

Zhang, Yan-Lei ;

Guo, Dong-Dong ;

Yan, Zhao-Lei ;

Guo, Shi-Huan ;

Wang, Yong-Qiang .

ORGANIC LETTERS, 2014, 16 (06) :1610-1613

[48] H8-BINOL chiral imidodiphosphoric acid catalyzed highly enantioselective aza-Friedel-Crafts reactions of pyrroles and enamides/imines [J].

Wu, Kun ;

Zhuo, Ming-Hua ;

Sha, Di ;

Fan, Yan-Sen ;

An, Dong ;

Jiang, Yi-Jun ;

Zhang, Suoqin .

CHEMICAL COMMUNICATIONS, 2015, 51 (38) :8054-8057

[49] Double Axially Chiral Bisphosphorylimides Catalyzed Highly Enantioselective and Efficient Friedel-Crafts Reaction of Indoles with Imines [J].

Wu, Kun ;

Jiang, Yi-Jun ;

Fan, Yan-Sen ;

Sha, Di ;

Zhang, Suoqin .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (02) :473-477

[50] Kinetic Resolution of Benzylamines via Palladium(II)-Catalyzed C-H Cross-Coupling [J].

Xiao, Kai-Jiong ;

Chu, Ling ;

Chen, Gang ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (24) :7796-7800

← 1 2 3 4 5 6 →