Journal
PURE AND APPLIED CHEMISTRY
Volume 80, Issue 5, Pages 807-817Publisher
WALTER DE GRUYTER GMBH
DOI: 10.1351/pac200880050807
Keywords
dicationic Pd catalyst; asymmetric 1,4-addition; arylboron compounds; transmetallation; enantioselection mechanism
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An enantioselective synthesis of cyclic and acyclic P-aryl ketone and aldehydes via Pd(II)-catalyzed 1,4-addition of Ar-m [m = B(OH)(2), BF3K, Si(OMe)(3), SiF3, BiAr2] to a,p-unsaturated ketones or aldehydes is described. The catalytic cycle-involves transmetallation between Ar-m and Pd complexes as a key process, the mechanism of which is discussed on the basis of characterization of the transmetallation intermediate and electronic effect of the substituents. The enantioselection mechanism and efficiency of a chiraphos ligand for structurally planar alpha,beta-unsaturated ketones are discussed on the basis of the X-ray structure of the catalyst and results of density functional theory (DFT) computational studies on the model of coordination of the Substrates to the phenylpalladium(II)/(S,S)-chiraphos intermediate.
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