Cleavage of Aromatic C-O Bonds via Intramolecular SNAr Reaction and Preparation of P,C,Axial-Stereogenic Menthyl Phosphine Derivatives.

Phosphine ligands with up to six chiral sites were prepared, starting from 2-phenylphenol, via O- and P-alkylation, cyclization, and coupling. The chirality was transferred from (L)-menthyl to phosphorus, α-carbon, and axis, to achieve excellent diastereoselectivities. During an intramolecular SNAr reaction with alkoxyl as the leaving groups, the C-O bond was converted to a C-C bond. Both phosphine boranes and oxides could be used for the conversions, affording a series of cyclic phosphines.