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Synthesis and application of new iminopyridine ligands in the enantioselective palladium-catalyzed allylic alkylation

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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DOI: 10.1016/j.molcata.2014.01.006

Abstract

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.

Item Type:Article
ID Code:9759
Status:Published
Refereed:Yes
Uncontrolled Keywords:Iminopyridine ligands, enantioselective catalysis, allylic substitution, palladium catalysis
Subjects:Area 03 - Scienze chimiche > CHIM/06 Chimica organica
Divisions:001 Università di Sassari > 01-a Nuovi Dipartimenti dal 2012 > Agraria
002 Altri enti e centri di ricerca del Nord Sardegna > CNR-Consiglio Nazionale delle Ricerche > Istituto di chimica biomolecolare, Sassari
Publisher:Elsevier
ISSN:1381-1169
eISSN:1873-314X
Deposited On:15 Apr 2014 10:11

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