Pyrrolidinopyridines in palladium-catalyzed allylic substitutions - Conformation of the ligand
2001 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 11, 2191-2195 p.Article in journal (Refereed) Published
The (R,R)-2-[(2,5-dimethylpyrrolidin-1-yl)methyl]pyridines 4, 5, and 6 carrying a 2-hydroxyalkyl, 2-alkoxyalkyl or 2-siloxyalkyl substituent in the 6-position of the pyridine ring were prepared and assessed in palladium-catalyzed allylations of 1,3-diphenylpropenyl acetate with malonate. All ligands having g-substituents with an S absolute configuration afforded the product with an R configuration in 80-84% ee, whereas those having substituents with an R absolute configuration gave the opposite product with a selectivity depending on the nature of the substituent (8-74% ee). It is believed that the enantioselectivity is dependent on the conformation of that substituent.
Place, publisher, year, edition, pages
2001. no 11, 2191-2195 p.
ligand design, asymmetric catalysis, palladium, nitrogen heterocycles, asymmetric catalysis, alkylation, complexes, pyrrolidines, allylation, induction, amine
IdentifiersURN: urn:nbn:se:kth:diva-20684ISI: 000169127700021OAI: oai:DiVA.org:kth-20684DiVA: diva2:339380
QC 201005252010-08-102010-08-10Bibliographically approved