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The design, preparation, structural and spectroscopic analyses of topologically unique and enantiomerically pure alkyl phosphonamides are described. In the case of alpha-ethyl and alpha-benzyl phosphonamides, the geometry of both the secondary and tertiary carbanions was determined to be planar through deprotonation/deuteration/alkylation experiments. Stereoselective alkylations of such systems proceeded in good yields and with high diastereoselectivities. The resulting alpha,alpha-alkylated phosphonamides were hydrolyzed to give the corresponding alpha,alpha-alkyl phosphonic acids with high degrees of enantiomeric purity.
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