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
收藏
页码：124 / 126
页数：3
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