Design of a new class of chiral quinoline–phosphine ligands. Synthesis and application in asymmetric catalysis

Pyridyl Phosphinites and Pyridyl Phosphites from Chiral Pyridyl Alcohols — A Modular Approach

“…The more rigid quinoline-containing ligand has also been used in palladium-catalysed aminations and alkylations of rac-1,3-diphenyl-2-propenyl acetate to afford products with moderate enantioselectivities. [27] The methoxybenzyl substituent in our ligands is situated far from the substrate in the palladiumϪallyl complex. Because of the bulkiness of the substituent, however, we believe that it prefers a pseudoequatorial position in the sixmembered chelate, which thereby increases the rigidity of the complex and, consequently, the chiral induction in the catalytic process.…”

Synthesis and Fluorescence Properties of 5,7-Diphenylquinoline and 2,5,7-Triphenylquinoline Derived from m-Terphenylamine

“…The preparation of the final product 2,5,7-triphenylquinoline was initially conducted in ethyl ether by adopting literature method as described for substituted 8-hydroxyquinolines [13]. Poor yields resulted in several attempts, which might be due to the poor solubility of 5,7-diphenylquinoline in ethyl ether.…”

P‐Chiral Monodentate Diamidophosphites − New and Efficient Ligands for Palladium‐Catalysed Asymmetric Allylic Substitution

“…Specifically, while the ees of product 11b in the allylic amination reaction were roughly equal (94% ee for QUIPHOS [27] and 95% ee for 3f), in the allylic alkylation reaction between 10 and dimethyl malonate, QUIPHOS (85% ee [27] ) and its analogues (R ϭ Me, Ph, tBu, CN, etc. [37] ) were outplayed by 3a (97% ee). Therefore, removal of the nitrogen donor centre and essential simplification of the ligand structure resulted in increased enantioselectivity and seem to represent a fruitful trend in chiral ligand design.…”