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

页码：2405 / 2410

页数：6

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