A. Marinetti et L. Ricard, SYNTHESIS AND CHARACTERIZATION OF SOME P-MENTHYLPHOSPHETANES, A NEW CLASS OF ELECTRON-RICH CHIRAL PHOSPHINES, Tetrahedron, 49(45), 1993, pp. 10291-10304
1-Menthyl substituted phosphetane oxides 4 and 6 are prepared either b
y starting from (menthyl)PCl2 and an appropriate olefin, or by reactin
g (menthyl)MgCl with a 1-chlorophosphetane. Highly selective alkylatio
n and halogenation reactions of the corresponding anions 4' afford alp
ha-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 provi
de an access to a wide range of optically pure phosphines of known ste
reochemistry.