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Synthesis 1994; 1994(12): 1272-1274
DOI: 10.1055/s-1994-25679
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Electrophilic Amination and Azidation of Chiral α-Alkyl Phosphonamides: Asymmetric Syntheses of α-Amino α-Alkyl Phosphonic Acids†

Stephen Hanessian* , Youssef L. Bennani
  • *Department of Chemistry, Université de Montréal, C.P. 6128, Centre-ville, Montréal, Québec H3C 3J7, Canada
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Publication Date:
25 April 2002 (online)

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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.