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.

Unexpected reversal of the enantioselectivity using chiral quinolylmethyl- and acridininyloxazokines as ligands for asymmetric palladium-catalyzed allylic alkylation / Pinna, Gérard Aimé; Saba, Antonio; Valenti, Raffaella; Chelucci, Giorgio Adolfo. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 11:19(2000), pp. 4027-4036. [10.1016/S0957-4166(00)00358-X]

Unexpected reversal of the enantioselectivity using chiral quinolylmethyl- and acridininyloxazokines as ligands for asymmetric palladium-catalyzed allylic alkylation

Pinna, Gérard Aimé;Saba, Antonio;Chelucci, Giorgio Adolfo
2000

Abstract

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.
Unexpected reversal of the enantioselectivity using chiral quinolylmethyl- and acridininyloxazokines as ligands for asymmetric palladium-catalyzed allylic alkylation / Pinna, Gérard Aimé; Saba, Antonio; Valenti, Raffaella; Chelucci, Giorgio Adolfo. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 11:19(2000), pp. 4027-4036. [10.1016/S0957-4166(00)00358-X]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11388/264107
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