Synthesis and crystallographic characterization of chiral bis-oxazoline-amides. Fine-tunable ligands for Pd-catalyzed asymmetric alkylations.
New chiral chelating C2 bis-oxazoline-amide ligands (1) exhibiting a highly flexible molecular structure have been prepared in high yield through a versatile synthetic pathway. Combined crystallographic, variable temperature (VT)-NMR, IR, and ESI-MS studies have been carried out to investigate the nature of the 1-Pd complexes that are effective tools in controlling the stereochemical outcome of Pd-catalyzed allylic alkylations (ee up to 98%).
Albano
Vincenzo Giulio
VG
Dipartimento di Chimica G. Ciamician, Università di Bologna. Via Selmi, 2 40126 Bologna, Italy.
Bandini
Marco
M
Monari
Magda
M
Marcucci
Eleonora
E
Piccinelli
Fabio
F
Umani-Ronchi
Achille
A
D000478:Alkylation; D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D008024:Ligands; D008958:Models, Molecular; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D000577:Amides; D008024:Ligands; D010080:Oxazoles; D010165:Palladium