146098-94-4Relevant articles and documents
The asymmetric synthesis of α-substituted α-methyl and α-phenyl phosphonic acids: Design, carbanion geometry, reactivity and preparative aspects of chiral alkyl bicyclic phosphonamides
Bennani, Youssef L.,Hanessian, Stephen
, p. 13837 - 13866 (2007/10/03)
The design, preparation, structural and spectroscopic analyses of topologically unique and enantiomerically pure alkyl phosphonamides are described. In the case of α-ethyl and α-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 α,α-alkylated phosphonamides were hydrolyzed to give the corresponding α,α-alkyl phosphonic acids with high degrees of enantiomeric purity.
Electrophilic amination and azidation of chiral α-alkyl phosphonamides: Asymmetric syntheses of α-amino α-alkyl phosphonic acids
Hanessian,Bennani
, p. 1272 - 1274 (2007/10/02)
Stereoselective electrophilic aminations of chiral non racemic α-alkyl phosphonamides, derived from N,N'-dimethyl (R,R)-1,2-diaminocyclohexane, 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.
