ChemInform Abstract: Stereospecific Synthesis of P‐Epimeric (RP1,RP2)‐Bis‐(O‐l‐ menthylphenylphosphonothionyl) Diselenide. A New Variant of the Stereoselective Staudinger Reaction.

Abstract

A n efficient procedure is described that leads to pure (SJ-0-1-menthylphenylthiophosphinate. The absolute configuration of this diastereomer was assigned by chemical correlation and confirmed by X-ray crystallography. The reaction of the isomer with phenyl azide, leading to amidate, is a new variant of the stereoselective Staudinger reaction. Addition of elemental selenium to the ( Sp)-thiophosphinate led to diastereomeric O-l-menthylphenylselenophosphonothioic acid, which was finally oxidized to the diastereomeric (Rpl ,Rp2)-bis-[0-1-menthylphenylphosphonothionyl] diselenide. The diselenide structure was unambiguously confirmed by 31P NMR spectroscopy.