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
收藏
页码：7112 / 7117
页数：6
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