Highly enantioselective Michael addition of malononitrile to alpha,beta-unsaturated ketones.
The highly enantioselective Michael addition of malononitrile to acyclic and cyclic alpha,beta-unsaturated ketones has been developed. The Michael reaction catalyzed by a primary amine derived from quinidine proceeded smoothly and provided the desired adducts with excellent enantioselectivities (83-97% ee).
Li
Xuefeng
X
National Engineering Research Center of Chiral Drugs and Key Laboratory of Asymmetric Synthesis & Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, The Chinese Academy of Sciences, Chengdu 610041, China.
Cun
Lingfeng
L
Lian
Chunxia
C
Zhong
Ling
L
Chen
Yingchun
Y
Liao
Jian
J
Zhu
Jin
J
Deng
Jingen
J
D000588:Amines / Q000737:chemistry; D002384:Catalysis; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry*; D008968:Molecular Conformation; D009570:Nitriles / Q000737:chemistry*; D013237:Stereoisomerism
D000588:Amines; D007659:Ketones; D009570:Nitriles; C000945:dicyanmethane