Tandem Photoredox-Chiral Phosphoric Acid Catalyzed Radical-Radical Cross-Coupling for Enantioselective Synthesis of 3-Hydroxyoxindoles

被引：13

作者：

Zhang, Yang ^{[1
]}

Ye, Dan ^{[1
]}

Shen, Lei ^{[1
]}

Liang, Kangjiang ^{[1
]}

Xia, Chengfeng ^{[1
]}

机构：

[1] Yunnan Univ, Yunnan Prov Ctr Res & Dev Nat Prod, Sch Chem Sci & Technol, Key Lab Med Chem Nat Resource,Minist Educ, Kunming 650091, Yunnan, Peoples R China

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 18期

基金：

中国国家自然科学基金;

关键词：

ASYMMETRIC-SYNTHESIS; OXINDOLE DERIVATIVES; ALPHA-ALKYLATION; 3-HYDROXY-2-OXINDOLES; HYDROXYLATION; ARYLATION; KETONES; ACCESS;

D O I：

10.1021/acs.orglett.1c02510

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A photochemical protocol that couples diarylamines and alpha-ketoesters to afford the chiral 3-hydroxyoxindoles through tandem photoredox and chiral phosphoric acid catalysis is developed. The reaction involves an enantioselective photochemical radical-radical cross-coupling process. The chiral phosphoric acid is discovered to play crucial roles by decreasing the reductive potentials of alpha-ketoesters and stereocontrolling the downstream asymmetric radical-radical cross-coupling via the formation of pentacoordinate complex.

引用

页码：7112 / 7117

页数：6

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