Stereocontrolled synthesis of homoallylic amines using phosphine oxides and isoxazolines

Article abstract of DOI:10.1016/S0040-4039(00)79895-9

Allylic diphenylphosphine oxides (7) undergo stereo selective 1,3-dipolar cycloadditions with nitrile oxides to give Δ²-isoxazolines (8). These may be reduced, also stereoselectively, to δ-amino-β-hydroxyalkyldiphenylphosphine oxides (9). Stereospecific Wittig-Horner type elimination of Ph₂PO₂-from amino alcohols (9) gives homoallylic amines (10) with controlled double bond geometry.