Organocatalytic enantioselective indole alkylations of alpha,beta-unsaturated ketones.
The C3-selective enantioselective Michael-type Friedel-Crafts alkylations of indoles with nonchelating alpha,beta-unsaturated alkyl ketones, catalysed by a chiral primary amine derived from natural cinchonine, were investigated. The reactions, in the presence of 30 mol% catalyst, were smoothly conducted at 0 to -20 degrees C. Moderate to good ee (47-89%) has been achieved.
Chen
Wei
W
Key Laboratory of Drug-Targeting of Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041, China.
Du
Wei
W
Yue
Lei
L
Li
Rui
R
Wu
Yong
Y
Ding
Li-Sheng
LS
Chen
Ying-Chun
YC
D000478:Alkylation; D000588:Amines / Q000737:chemistry; D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry; D018360:Crystallography, X-Ray; D007097:Imines / Q000737:chemistry; D007211:Indoles / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
D000588:Amines; D002930:Cinchona Alkaloids; D007097:Imines; D007211:Indoles; D007659:Ketones; C010086:cinchonine