title: Synthesis and Resolution of Quinazolinone Atropisomeric Phosphine Ligands(,).
abstract: The syntheses of 2-methyl-3-[2'-(diphenylphosphino)phenyl]-4(3H)-quinazolinone (MPQ, 1a) and methyl-substituted analogues were achieved in good yield by coupling N-acetylanthranilic acid with the corresponding phosphinoanilines. Resolution of ligand 1bwas achieved using (-)-di-&mgr;-chlorobis[(S)-dimethyl-(1-phenylethyl)aminato-C(2),N]dipalladium(II) (5). The resulting crystalline complex (S,R)-6 served to unambiguously assign the absolute configuration of antipode (R)-(-)-1b. A practical resolution of this series of ligands 1a-c was accomplished using the (benzenesulfonyl)hydrazone derivative of camphorsulfonic acid (7) as a resolving agent.
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139.
authors.forename: Xuedong
authors.initials: X
authors.lastname: Dai
authors.forename: Audrey
authors.initials: A
authors.lastname: Wong
authors.forename: Scott C.
authors.initials: SC
authors.lastname: Virgil