Asymmetric Synthesis of 3-Lactone-Substituted 2-Oxindoles with Vicinal Quaternary Carbon Centers through Vinylogous Conjugate Addition

被引：4
作者：
Li, Zegong [1 ]
Zeng, Zi [1 ]
Tang, Qi [1 ]
Zhong, Ziwei [1 ]
Liu, Xiaohua [1 ]
Feng, Xiaoming [1 ]
机构：
[1] Sichuan Univ, Minist Educ, Coll Chem, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
来源：
SYNLETT | 2023年 / 34卷 / 20期
基金：
中国国家自然科学基金;
关键词：
asymmetric catalysis; nickel catalysis; ligands; bromooxindoles; lactones; vinylogous addition; CONSTRUCTION; 3-BROMOOXINDOLES; CYCLIZATION; ALKYLATION; 3-HALOOXINDOLES; CYCLOADDITION; STEREOCENTERS; ALLYLATION; INHIBITORS; AMINATION;
D O I：
10.1055/a-2066-2879
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new method has been developed for constructing vicinal quaternary stereocenters with an oxindole-butanolide hybrid framework through asymmetric vinylogous addition of a siloxyfuran to an indol-2-one in the presence of a readily available N,N'-dioxide-Ni(OTf)(2) complex catalyst. Various oxindole-lactones were obtained in up to 98% yield with >19:1 dr and 97% ee under mild reaction conditions. A possible transition-state model is proposed to explain the origin of the asymmetric induction.
引用
收藏
页码：2405 / 2410
页数：6
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