Steric versus electronic effects of the ligand in the enantioselective palladium-catalyzed allylic alkylation with chiral oxazolinylpyridines

Authors
Chelucci, G Deriu, S Pinna, GA Saba, A Valenti, R
Citation
G. Chelucci et al., Steric versus electronic effects of the ligand in the enantioselective palladium-catalyzed allylic alkylation with chiral oxazolinylpyridines, TETRAHEDR-A, 10(19), 1999, pp. 3803-3809
Citations number
20
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
19
Year of publication
1999
Pages
3803 - 3809
Database
ISI
SICI code
0957-4166(19990924)10:19<3803:SVEEOT>2.0.ZU;2-A
Abstract
Chiral oxazolinylpyridines bearing an oxazolinyl [bis(oxazolinyl)pyridines] or a cyano group in the 6-position of the pyridine ring were prepared and assessed in the enantioselective palladium-catalyzed allylic substitution o f 1,3-diphenylprop-2-enyl acetate with dimethyl malonate. The electronic an d steric properties of substituents hardly affected either the catalytic ac tivity or the enantioselectivity of the substitution reaction. Enantioselec tivities up to 94% were obtained. (C) 1999 Elsevier Science Ltd. All rights reserved.