Reactions of Chiral Phosphorous Acid Diamides

Abstract

Abstract Chiral phosphorous acid diamides were prepared from chiral C2 diamines via the sequential addition of PCl3 and H2O. Alternatively, addition of PCI3 and hydrogen sulfide yieded the analogous thiophosphorous acid diamides. Deprotonation of the phosphorous acids under a variety of conditions gave the anions which reacted smoothly with alkyl halides to give phosphonamides in good yield. Reaction of the anions with aldehydes gave α-hydroxy-phosphonamides in good yield and with modest diastereoselectivity (1:1 - 25:1 ds). Treatment of the phosphorous acids with trialkylsilyl triflates and Hunnig's base gave the product of O-silylation.