Asymmetric 1,4-addition of arylboronic acids to 2,3-dihydro-4-pyridones catalyzed by axially chiral NHC-Pd(II) complexes.
Axially chiral cis-chelated bidentate bis(N-heterocyclic carbene)-palladium(II) complexes are effective catalysts for the asymmetric conjugate addition of arylboronic acids to 2,3-dihydro-4-pyridones, producing the synthetically and biologically important 2-aryl-4-piperidones in moderate-to-high yields (up to 96%) along with excellent enantioselectivities (up to >99.5% ee) in most cases under mild conditions.
Xu
Qin
Q
Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, and 130 MeiLong Road, Shanghai 200237, People's Republic of China.
Zhang
Rui
R
Zhang
Tao
T
Shi
Min
M
D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D010165:Palladium / Q000737:chemistry; D010881:Piperidones / Q000138:chemical synthesis*; D011728:Pyridones / Q000737:chemistry*; D013237:Stereoisomerism
D001897:Boronic Acids; D010881:Piperidones; D011728:Pyridones; D010165:Palladium