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

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