A Concise Stereoselective Route to C-and P-Chirogenic Hydroxypropyl Phosphines by Ring-Opening of Optically Active Oxaphospholane-2-oxide

摘要

A facile,stereoselective method for the synthesis of both carbon-and P-chirogenic phosphine oxides and phosphines bearing a hydroxyl chelating arm was developed.A carefully designed oxaphospholane was constructed via tandem Arbuzov-intramolecular cyclization reaction,using commercially available compounds.Regioselective ring opening alkylation/arylation provided optically active phosphine oxides within two synthetic steps.An additional step of stereospecific deoxygenation produced P-chirogenic tertiary phosphines in high dr.