Enantioselective Friedel-Crafts reaction of 4,7-dihydroindoles with β-CF3-β-disubstituted nitroalkenes

被引：39

作者：

Wu, Hao ^{[1
]}

Liu, Ren-Rong ^{[1
]}

Shen, Chong ^{[1
]}

Zhang, Ming-Di ^{[1
]}

Gao, Jianrong ^{[1
]}

Jia, Yi-Xia ^{[1
]}

机构：

[1] Zhejiang Univ Technol, Coll Chem Engn, Hangzhou 310014, Zhejiang, Peoples R China

来源：

Organic Chemistry Frontiers | 2015年 / 2卷 / 02期

基金：

中国国家自然科学基金;

关键词：

CARBON QUATERNARY STEREOCENTERS; CATALYTIC ASYMMETRIC-SYNTHESIS; CHIRAL PHOSPHORIC-ACIDS; STEREOSELECTIVE CONSTRUCTION; BRONSTED ACIDS; ALKYLATION; INDOLES; ENONES; ACCESS; DERIVATIVES;

D O I：

10.1039/c4qo00265b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Using a Ni(ClO4)(2)-bisoxazoline complex as a catalyst, Friedel-Crafts alkylations of 4,7-dihydroindoles with beta-CF3-beta-disubstituted nitroalkenes were carried out with high enantioselectivities (up to 91%) to give alkylated dihydroindoles bearing trifluoromethylated all-carbon quaternary stereocenters in good yields. The corresponding chiral C2 alkylated indoles were obtained with complete preservation of enantiomeric purity by oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ).

引用

页码：124 / 126

页数：3

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