Enantioselective Friedel-Crafts alkylation of indoles with trifluoropyruvates catalyzed by chiral Cu(II) complex bearing binaphthyl-proline hybrid ligands

被引：1

作者：

Yao, Chao ^{[1
]}

Hou, Jiaqi ^{[1
]}

Cai, Qihang ^{[1
]}

Chen, Yaoqi ^{[1
]}

Wang, Chao ^{[1
]}

Liang, Jiemian ^{[1
]}

Jiao, Zilin ^{[1
]}

Li, Lin ^{[1
]}

Li, Yue-Ming ^{[1
]}

机构：

[1] Nankai Univ, Coll Pharm, State Key Lab Med Chem Biol, Tianjin, Peoples R China

来源：

TETRAHEDRON | 2024年 / 154卷

基金：

中国国家自然科学基金;

关键词：

Proline; Binaphthyl; Copper (II); Friedel-crafts alkylation; ASYMMETRIC FLUORINATION; PRIVILEGED STRUCTURES; TRIFLUOROMETHYLATION; HIV-1; FUNCTIONALIZATION; HYDROXYALKYLATION; DESIGN;

D O I：

10.1016/j.tet.2024.133874

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and efficient catalyst system for asymmetric Friedel-Crafts alkylation of indoles with trifluoropyruvates was reported. The chiral ligands took the advantages of both the proline and the binaphthyl moieties, and the in situ prepared Cu(II) catalyst showed good substrate tolerance in the reactions. Indoles bearing different substituents could be tolerated, and the desired products could be obtained in up 99 % yields and up to 98 % ee. Especially, the reactions could be carried out in gram scale without the loss of stereoselectivity, and some of products were able to achieve 99 % ee after simple crystallization.

引用

页数：7

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