Palladium-catalyzed reactions .1. Palladium-catalyzed enantioselective hydrophenylation and hydrohetarylation of bicyclo[2.2.1]hept-2-ene: Influence of the chiral ligand, the leaving group, and the solvent

The use of optically active biaryl bisphosphanes 10-12, a diphenylphosphanylphenyloxazoline 8, and a (beta-N-sulfonyl-aminomethyl)bisdiphenylphosphane 7 as ligands in the Pd-catalyzed Heck-type hydroarylation of norbornene (1) with phenyl 2 and various hetaryl derivatives 3-5 leads exclusively to the formation of exo-2-(het)arylnorbornanes 6 with asymmetric inductions of up to 86.4% ee, In addition to an investigation into the effects of different chiral ligands, a systematic study has been made of the influence of various (het)aryl compounds, leaving groups, and solvents on the chemical and optical yields of this reductive arylation.