Highly enantioselective michael addition of cyclic 1,3-dicarbonyl compounds to alpha,beta-unsaturated ketones.
[reaction: see text] The highly enantioselective Michael addition of 1,3-cyclic dicarbonyl compounds to alpha,beta-unsaturated ketones was reported to be catalyzed by an organic primary amine derived from quinine. A chiral anticoagulant drug, (S)-warfarin, was directly prepared in 96% ee, and other related important adducts were also obtained in excellent enantioselectivity (89-99% ee).
Xie
Jian-Wu
JW
Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province and Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, China.
Yue
Lei
L
Chen
Wei
W
Du
Wei
W
Zhu
Jin
J
Deng
Jin-Gen
JG
Chen
Ying-Chun
YC
D000447:Aldehydes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry; D000925:Anticoagulants / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D007659:Ketones / Q000737:chemistry*; D008956:Models, Chemical; D008958:Models, Molecular; D011803:Quinine / Q000737:chemistry; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D000588:Amines; D000925:Anticoagulants; D007659:Ketones; D012997:Solvents; D011803:Quinine