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

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.

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DOI: 10.1016/S0957-4166(00)00358-X

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.

Item Type:Article
ID Code:317
Status:Published
Refereed:Yes
Uncontrolled Keywords:Enantioselectivity, chiral quinolylmethyloxazolines, acridininyloxazokines, allylic alkylation
Subjects:Area 03 - Scienze chimiche > CHIM/08 Chimica farmaceutica
Divisions:001 Università di Sassari > 01 Dipartimenti > Chimica
001 Università di Sassari > 01 Dipartimenti > Farmaco, chimico, tossicologico
Publisher:Pergamon / Elsevier
ISSN:0957-4166
Copyright Holders:© 2000 Elsevier Science
Deposited On:18 Aug 2009 10:02

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