Solinas, Maurizio and Sechi, Barbara and Chelucci, Giorgio Adolfo and Baldino, Salvatore and Pedro, José R. and Blay, Gonzalo (2014) Synthesis and application of new iminopyridine ligands in the enantioselective palladium-catalyzed allylic alkylation. Journal of molecular catalysis A: Chemical, Vol. 385 , p. 73-77. ISSN 1381-1169. eISSN 1873-314X. Article.
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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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