Title of article :
Bisphenylene homologues of BINOL-based phosphoramidites: synthesis, stereostructure, and application in catalysis
Author/Authors :
Mikl??ov?، نويسنده , , Natalia and Jul?nek، نويسنده , , Ond?ej and Me?kov?، نويسنده , , Michaela and Setni?ka، نويسنده , , Vladim?r and Urbanov?، نويسنده , , Marie and Putala، نويسنده , , Martin، نويسنده ,
Abstract :
Bis-ortho- and bis-meta-phenylene homologues of BINOL-based N,N-dimethylphosphoramidites were prepared from the corresponding diols by treatment with hexamethyltriaminophosphane. Phosphoramidites derived from bulkier secondary amines were synthesized by 5-phenyl-1H-tetrazole-promoted amine exchange. All the phosphoramidites were obtained as single diastereomers. Their configurations at the C(naphthyl)–C(phenyl) axes were determined by vibrational circular dichroism (VCD) spectroscopy. Preliminary testing of the ligands in copper-catalyzed conjugate addition of diethylzinc to acyclic enones and nitrostyrene gave the corresponding products in up to 74% ee.
