Cleavage of Aromatic C-O Bonds via Intramolecular S N Ar 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 - and -alkylation, cyclization, and coupling. The chirality was transferred from ()-menthyl to phosphorus, α-carbon, and axis, to achieve excellent diastereoselectivities. During an intramolecular SAr 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.