Atroposelective Construction of Arylindoles by Chiral Phosphoric Acid-Catalyzed Cross-Coupling of Indoles and Quinones

Lu, Dong-Liang1; Chen, Ye-Hui2,3; Xiang, Shao-Hua2,4; Yu, Peiyuan2,3; Tan, Bin2,3; Li, Shaoyu2,4

2019-08-02

10.1021/acs.orglett.9b02143

ORGANIC LETTERS   影响因子和分区

1523-7060

1523-7052

Structurally novel atropisomeric arylindole frameworks have been successfully constructed through chiral phosphoric acid-catalyzed asymmetric cross-coupling of indoles and quinone derivatives in a precise regioselective manner. This approach features high convergence and functional group tolerance to efficiently deliver diverse heteroaryl atropisomers with excellent enantiocontrol. The dominant formation of axial chirality but not central chirality, as the major unmet challenge for this type of reactions, was conquered by the rational and accurate modulation of the electronic and steric effects on both coupling partners. Preliminary investigation demonstrated the practicality of such axially chiral arylindoles as chiral ligands in asymmetric catalysis.

SCI ; IC ; CCR

英语

NI期刊

通讯

Shenzhen Special Funds for the Development of Biomedicine, Internet, New Energy and New Material Industries[JCYJ20170412151701379] ; Shenzhen Special Funds for the Development of Biomedicine, Internet, New Energy and New Material Industries[KQJSCX20170328153203]

Chemistry

Chemistry, Organic

WOS:000480371600048

AMER CHEMICAL SOC

CHEMISTRY

Web of Science

1.Gannan Normal Univ, Key Lab, Jiangxi Univ Funct Mat Chem, Ganzhou 341000, Peoples R China
2.Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Peoples R China
3.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Peoples R China
4.Southern Univ Sci & Technol, Acad Adv Interdisciplinary Studies, Shenzhen 518055, Peoples R China

Lu, Dong-Liang,Chen, Ye-Hui,Xiang, Shao-Hua,et al. Atroposelective Construction of Arylindoles by Chiral Phosphoric Acid-Catalyzed Cross-Coupling of Indoles and Quinones[J]. ORGANIC LETTERS,2019,21(15):6000-6004.

Lu, Dong-Liang,Chen, Ye-Hui,Xiang, Shao-Hua,Yu, Peiyuan,Tan, Bin,&Li, Shaoyu.(2019).Atroposelective Construction of Arylindoles by Chiral Phosphoric Acid-Catalyzed Cross-Coupling of Indoles and Quinones.ORGANIC LETTERS,21(15),6000-6004.

Lu, Dong-Liang,et al."Atroposelective Construction of Arylindoles by Chiral Phosphoric Acid-Catalyzed Cross-Coupling of Indoles and Quinones".ORGANIC LETTERS 21.15(2019):6000-6004.