Remote electronic control of the ligand in the enantioselective palladium-catalyzed allylic alkylation with chiral oxazolinylpyridines

Authors
Chelucci, G Deriu, SP Saba, A Valenti, R
Citation
G. Chelucci et al., Remote electronic control of the ligand in the enantioselective palladium-catalyzed allylic alkylation with chiral oxazolinylpyridines, TETRAHEDR-A, 10(8), 1999, pp. 1457-1464
Citations number
20
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
8
Year of publication
1999
Pages
1457 - 1464
Database
ISI
SICI code
0957-4166(19990423)10:8<1457:RECOTL>2.0.ZU;2-B
Abstract
New chiral oxazolinylpyridines bearing electron-donating and withdrawing gr oups lin the 4-position of the pyridine ring have been prepared and assesse d in the enantioselective palladium catalyzed allylic substitution of 1,3-d iphenylprop-2-enyl acetate with dimethyl malonate. The electronic propertie s of substituents strongly affect the catalytic activity and only slightly affect the enantioselectivity of the substitution reaction. Enantioselectiv ity up to 93% was obtained. (C) 1999 Elsevier Science Ltd. All rights reser ved.