Chelucci, Giorgio Adolfo and Pinna, Gérard Aimé and Saba, Antonio and Valenti, Raffaella (2000) Unexpected reversal of the enantioselectivity using chiral quinolylmethyl- and acridininyloxazokines as ligands for asymmetric palladium-catalyzed allylic alkylation. Tetrahedron: Asymmetry, Vol. 11 (19), p. 4027-4036. ISSN 0957-4166. Article.
New chiral quinolylmethyloxazolines and acridininyloxazolines were prepared and assessed in the enantioselective palladium-catalyzed allylic substitution of 1,3-diphenylprop-2-enyl acetate with dimethyl malonate. The introduction of a benzo-fused substituent on the pyridine ring not containing the chiral backbone resulted in the switch of the expected chiral sense of enantioselection of the reaction. Enantiomeric excesses up to 78% were obtained.
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