Electrophilic Amination and Azidation of Chiral α-Alkyl Phosphonamides: Asymmetric Syntheses of α-Amino α-Alkyl Phosphonic Acids†

Abstract
Stereoselective electrophilic aminations of chiral non racemic α-alkyl phosphonamides, derived from N,N′-dimethyl (R,R)-1,2-diamino-cyclohexane, proceed with moderate to excellent enantioselectivities. The products are hydrolyzed and reduced to the corresponding α-alkyl α-amino phosphonic acids. The sense of asymmetric induction was confirmed by X-ray crystal structure analysis.

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