Stereogenic Phosphorus

This review is concerned with stereogenic phosphorus sites as they occur in phosphorus compounds owning the several stages of coordination. The nature of the stereogenic phosphorus, the modes of generation of compounds containing such stereogenic phosphorus, and the stereochemistry associated with their reactions are surveyed. In particular, tricoordinated (phosphine, phosphite, phosphonite and phosphinite) phosphorus, tetracoordinated (phosphonium, phosphonate, phosphinate, phosphine oxide) phosphorus, pentacoordinated (phosphoranes and oxyphosphoranes) phosphorus, and hexacoordinated (cationic and anionic) phosphorus systems are reviewed. In addition to efforts recently reported concerning such compounds, historical perspectives and potential topics for continuing research are presented. Experimental procedures for the preparation of representative chiral species of each type are given.