Catalytic Asymmetric Friedel-Crafts Alkylation of Indole via In Situ Generated Indol-2-one

被引：3

作者：

Fei, Yuanai ^{[1
]}

Hou, Jun ^{[1
]}

Song, Huiying ^{[1
]}

Yang, Mei-li ^{[2
]}

Lei, Pan ^{[1
]}

Ge, Xiayu ^{[1
]}

Wei, Hongbo ^{[1
]}

Xu, Yuanzhen ^{[1
]}

Xie, Weiqing ^{[1
]}

机构：

[1] Northwest A&F Univ, Coll Chem & Pharm, Shaanxi Key Lab Nat Prod & Chem Biol, 22 Xinong Rd, Yangling 712100, Shaanxi, Peoples R China

[2] Baoji Univ Arts & Sci, Coll Chem & Chem Engn, Shaanxi Key Lab Phytochem, Baoji 721013, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 26卷 / 12期

基金：

中国国家自然科学基金;

关键词：

3-bromooxidole; enantioselective Friedel-Crafts alkylation; folicanthine; indoles; 3-substituted; 3-indolyloxindole; ENANTIOSELECTIVE TOTAL-SYNTHESIS; CARBON QUATERNARY STEREOCENTERS; CONCISE TOTAL-SYNTHESIS; PREPARING EPIDITHIODIOXOPIPERAZINES; CONSTRUCTION; OXINDOLES; 3-HALOOXINDOLES; 3-BROMOOXINDOLES; METABOLITES; ALDEHYDES;

D O I：

10.1002/ejoc.202300122

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An asymmetric Friedel-Crafts alkylation of indole with in situ generated indol-2-one from functionalized 3-bromooxinidole catalyzed by chiral N,N'-dioxide/Ni(BF4)(2) has been developed. This protocol provides an efficient route to stereoselective construction of a series of 3-substituted 3'-indolyloxindoles bearing a quaternary carbon center in excellent yields and enantioselectivities (up to 99 % ee). In addition, the conversion of the resulted 3-substituted 3'-indolyloxindole to the key intermediate for the formal synthesis of (+)-folicanthine was also demonstrated.

引用

页数：5

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