Highly enantioselective Michael addition of cyclopentanone with chalcones via novel di-iminium mechanism.
The highly efficient asymmetric Michael addition reactions of cyclopentanone with chalcones were catalyzed by a simple and commercially available chiral 1,2-diaminocyclohexane-hexanedioic acid, and exhibited good yields (up to 92%) and excellent enantioselectivities (up to 99% ee). A new di-iminium mechanism for the reaction was proposed.
Wang
Junfeng
J
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, 38 Xueyuan Road, 100191, Beijing, PR China.
Wang
Xin
X
Ge
Zemei
Z
Cheng
Tieming
T
Li
Runtao
R
D002384:Catalysis; D002599:Chalcone / Q000737:chemistry*; D003517:Cyclopentanes / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D013696:Temperature
D003517:Cyclopentanes; C007201:cyclopentanone; D002599:Chalcone