Generation of metal phosphinites by the reaction of Se-alkyl phosphinoselenoates with organometallics and its application to the synthesis of optically active organophosphorus compounds^†

Reaction of Se-Alkyl phosphinoselenoates with organometallics resulted in a selective attack on the selenium atom. Sequential treatment of optically active Se-benzyl t-butylphenylphosphinoselenoate with PhLi and then with electrophiles, such as alkyl halides, an α,β-unsaturated ester, and chalcogen atoms gave optically active phosphorus compounds in 5–91% yields and in high optical yields, with retention of configuration at the phosphorus atom, along with a quantitative yield of benzyl phenyl selenide.