Organocatalytic C3-selective Friedel-Crafts alkylations of indoles with alpha,beta-unsaturated ketones.
The use of an equimolar amount of pyrrolidine and HClO4 (30 mol%) was found to be effective in promoting the conjugate addition of indoles to (E)-alpha,beta-unsaturated ketones, affording the corresponding beta-indolyl ketones in excellent yields.
Li
Dong-Ping
DP
Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, China.
Guo
Ying-Cen
YC
Ding
Yu
Y
Xiao
Wen-Jing
WJ
D000478:Alkylation; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D007211:Indoles / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis*; D015394:Molecular Structure; D010472:Perchlorates / Q000737:chemistry; D011759:Pyrrolidines / Q000737:chemistry; D013237:Stereoisomerism
D007211:Indoles; D007659:Ketones; D010472:Perchlorates; D011759:Pyrrolidines; D002244:Carbon; C032519:pyrrolidine