Enantioselective Michael reaction of α-alkyl-β-keto esters and enones under multifunctional catalysis.
An efficient approach for the enantioselective Michael additions of β-alkyl-β-keto esters to β-substituted α,β-unsaturated ketones has been developed. The Michael products could be obtained in good to excellent yields (75-98%) with excellent diastereoselectivities (up to >99:1 dr) and enantioselectivities (up to 96% ee) and could easily be transformed into a synthetically useful hexahydrophenanthrene structure under mild conditions in good yield.
Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China.
Juanjuan
J
Yang
Wenjun
W
Li
Zhichao
Z
Jin
Xinmiao
X
Liang
Jinxing
J
Ye
D000475:Alkenes / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D004952:Esters; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D010616:Phenanthrenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D004952:Esters; D007659:Ketones; D010616:Phenanthrenes