249304-86-7Relevant academic research and scientific papers
The preparation and resolution of 2-phenyl-Quinazolinap, A new atropisomeric phosphinamine ligand for asymmetric catalysis
McCarthy, Mary,Goddard, Richard,Guiry, Patrick J.
, p. 2797 - 2807 (1999)
The preparation and resolution of an axially chiral quinazoline-containing phosphinamine ligand is described. The biaryl linkage was formed in a Pd-catalysed coupling of 4-chloro-2-phenylquinazoline 10 with 2-methoxy-1-naphthylboronic acid 11. Demethylati
Preparation and resolution of a modular class of axially chiral quinazoline-containing ligands and their application in asymmetric rhodium-catalyzed olefin hydroboration
Connolly, David J.,Lacey, Patrick M.,McCarthy, Mary,Saunders, Cormac P.,Carroll, Anne-Marie,Goddard, Richard,Guiry, Patrick J.
, p. 6572 - 6589 (2007/10/03)
The preparation and resolution of a series of axially chiral quinazoline-containing ligands is described in which the key steps are the metal-catalyzed naphthyl-phosphorus bond formation, the naphthalene-quinazoline Suzuki coupling, and the preparation of the Suzuki electrophilic components from the corresponding imidate and anthranilic acid. Diastereomeric palladacycles derived from the racemic phosphinamines and (+)-di-μ-chlorobis[(R)- dimethyl(1-(1-naphthyl)ethyl)-aminato-C2,N]dipalladium(II) were separated by fractional crystallization. The configuration of the resulting diastereomers was determined by X-ray crystallographic analysis. Displacement of the resolving agent by reaction with 1,2-bis(diphenylphosphino)ethane afforded enantiopure ligand in each case. Their rhodium complexes were prepared and applied in the enantioselective hydroboration of a range of vinylarenes. The quinazolinap catalysts were found to be extremely active, giving excellent conversions, good to complete regioselectivities, and the highest enantioselectivities obtained to date for several members of the vinylarene class, including cis-β-methylstyrene (97%), cis-stilbene (99%), and indene (99.5%).
Synthesis of 4-(2-diphenylphosphino-1-naphthyl)-2-phenylquinazoline; A potential P-N chelating ligand for asymmetric catalysis
Gautheron Chapoulaud,Audoux,Ple,Turck,Queguiner
, p. 9005 - 9007 (2007/10/03)
We describe a multistep synthesis leading in a good yield to the title compound. The biaryl linkage was formed in a Pd-catalysed coupling of 2-phenyl-4-chloroquinazoline with 2-methoxy-1-naphthylboronic acid. A further metal-catalysed reaction gave the formation of the naphthylphosphorus bond allowing us to obtain the required phosphonimine ligand 1 as the racemate.
