Enantioselective organocatalytic michael addition of malonates to alpha,beta-unsaturated ketones.
A novel type of primary amine thiourea organocatalysts derived from 1,2-diaminocyclohexane and 9-amino (9-deoxy) cinchona alkaloid was developed into asymmetric Michael addition of malonates to enones. A series of cyclic and acyclic enones could react very well with different malonates in the presence of 4 with 0.5-10 mol % catalyst loading affording chiral Michael adducts with excellent yields and ee values.
Li
Pengfei
P
Dalian Institute of Chemical Physics, Chinese Academy of Science, 457 Zhongshan Road, Dalian 116023, P. R. China.
Wen
Shigang
S
Yu
Feng
F
Liu
Qiaoxia
Q
Li
Wenjun
W
Wang
Yongcan
Y
Liang
Xinmiao
X
Ye
Jinxing
J
D002930:Cinchona Alkaloids / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry*; D008314:Malonates / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D002930:Cinchona Alkaloids; D007659:Ketones; D008314:Malonates