Synthesis of N-Substituted 4-Quinolones via Palladium-Catalyzed Enantioselective C-N Coupling and Base-Promoted Reactions

被引：6

作者：

Pu, Xiaoyun ^{[1
]}

Zhang, Yaqi ^{[1
]}

He, Xiaobo ^{[1
]}

Zhang, Xinhuan ^{[1
]}

Jiang, Long ^{[2
]}

Cao, Rihui ^{[1
]}

Kin Tse, Man ^{[3
]}

Qiu, Liqin ^{[1
]}

机构：

[1] Sun Yat sen Univ, Sch Chem, Guangdong Prov Key Lab Chiral Mol & Drug Discovery, Guangzhou 510006, Peoples R China

[2] Sun Yat sen Univ, Instrumental Anal & Res Ctr, Guangzhou 510275, Peoples R China

[3] Guangzhou Lee & Man Technol Co Ltd, 8 Huanshi Ave South, Guangzhou 511458, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2023年 / 365卷 / 08期

关键词：

Palladium; Ferrocene bisphosphine ligand; Enantioselective C-N coupling; Base-promoted C-N coupling; N-Substituted; 4-quinolones; ACTIVE ATROPISOMERIC ANILIDES; METAL-FREE SYNTHESIS; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; AXIAL CHIRALITY; CONSTRUCTION; DERIVATIVES; CYCLIZATION; ALLYLATION; ARYLATION;

D O I：

10.1002/adsc.202300153

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A highly efficient palladium-catalyzed asymmetric synthesis of N-substituted 4-quinolones was developed via C-N coupling reaction. Various chiral quinolones were readily obtained with desirable enantioselectivity (up to 95% ee) and excellent yield (up to 99%), enabled by a simple system of palladium acetate and chiral ferrocene bisphosphine as auxiliary ligand. The corresponding racemic derivatives can also be synthesized by a transition metal-free strategy of potassium hydroxide in DMSO. The influence of temperature on the configurational stability of these C-N axially chiral compounds was also investigated. The efficient functionalization at 3-position further expands the application range of this synthetic technique.

引用

页码：1152 / 1157

页数：6

共 55 条

[11] The Challenge of Atropisomerism in Drug Discovery [J].

Clayden, Jonathan ;

Moran, Wesley J. ;

Edwards, Paul J. ;

LaPlante, Steven R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (35) :6398-6401

[12] C-N atropopure compounds: New directions [J].

Colobert, Francoise ;

Shi, Bing-Feng .

CHEM CATALYSIS, 2021, 1 (03) :483-485

[13] Synthesis and resolution of quinazolinone atropisomeric phosphine ligands [J].

Dai, XD ;

Wong, A ;

Virgil, SC .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08) :2597-2600

[14] Synthesis and evaluation of quinoline carboxyguanidines as antidiabetic agents [J].

Edmont, D ;

Rocher, R ;

Plisson, C ;

Chenault, J .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (16) :1831-1834

[15] Enantioselective Atropisomeric Anilides Synthesis via Cu-Catalyzed Intramolecular Adjacent C-N Coupling [J].

Fan, Xiaozhong ;

Zhang, Xue ;

Li, Chunyu ;

Gu, Zhenhua .

ACS CATALYSIS, 2019, 9 (03) :2286-+

[16] Enantioselective Synthesis of N-C Axially Chiral Compounds by Cu-Catalyzed Atroposelective Aryl Amination [J].

Frey, Johanna ;

Malekafzali, Alaleh ;

Delso, Isabel ;

Choppin, Sabine ;

Colobert, Francoise ;

Wencel-Delord, Joanna .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (23) :8844-8848

[17] Atropisomeric Phosphine Ligands Bearing C-N Axial Chirality: Applications in Enantioselective Suzuki-Miyaura Cross-Coupling Towards the Assembly of Tetra-ortho-Substituted Biaryls [J].

Gan, Kin Boon ;

Zhong, Rong-Lin ;

Zhang, Zhen-Wei ;

Kwong, Fuk Yee .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (32) :14864-14873

[18] Phytotoxins from the leaves of Ruta graveolens [J].

Hale, AL ;

Meepagala, KM ;

Oliva, A ;

Aliotta, G ;

Duke, SO .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2004, 52 (11) :3345-3349

[19] Catalytic Enantioselective Synthesis of N-C Axially Chiral Phenanthridin-6-one Derivatives [J].

Hirata, Tomoaki ;

Takahashi, Isao ;

Suzuki, Yuya ;

Yoshida, Hiroaki ;

Hasegawa, Hiroshi ;

Kitagawa, Osamu .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (01) :318-323

[20] The marinopyrroles, antibiotics of an unprecedented structure class from a marine Streptomyces sp. [J].

Hughes, Chambers C. ;

Prieto-Davo, Alejandra ;

Jensen, Paul R. ;

Fenical, William .

ORGANIC LETTERS, 2008, 10 (04) :629-631

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