| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 65723 | Journal of Molecular Catalysis A: Chemical | 2014 | 5 Pages |
•New chiral iminopyridines were obtained from pyridyl and quinolinyl aldehydes.•New chiral iminopyridines were obtained from a variety of chiral or achiral amines.•New ligands were assessed in the enantioselective Pd-catalyzed allylic substitution.•1,3-Diphenylprop-2-enylmalonate was obtained with enantioselectivities up to 62% ee.
A variety of iminopyridines were obtained by condensation of chiral amines with pyridine-2-carboxaldehyde and quinoline-8-carbaldehyde, or of aminoalkylpyridine derivatives with chiral ketones. These ligands were assessed in the enantioselective palladium catalyzed allylic substitution of 1,3-diphenylprop-2-enyl acetate with dimethyl malonate affording the product dimethyl 1,3-diphenylprop-2-enylmalonate in good yields and moderate enantioselectivities (up to 62% ee). Catalytic activity and enantioselectivity were found to be highly dependent upon the steric properties of the ligands. The best enantioselectivity (62% ee) was obtained by an iminopyridine based on a camphane skeleton.
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