Synthesis and characterization of some P-menthylphosphetanes, a new class of electron-rich chiral phosphines

Article abstract of DOI:10.1016/S0040-4020(01)80558-5

1-Menthyl substituted phosphetane oxides 4 and 6 are prepared either by starting from (menthyl)PCl₂ and an appropriate olefin, or by reacting (menthyl)MgCl with a 1-chlorophosphetane. Highly selective alkylation and halogenation reactions of the corresponding anions 4' afford α-substituted derivatives in diastereomerically pure form. Reductions of the phosphetane oxides with HSiCl₃.Et₃N proceed with retention of configuration about the phosphorus atom. The described procedure provide an access to a wide range of optically pure phosphines of known stereochemistry.