98048-99-8Relevant articles and documents
Conversion of nitriles to 1-aminophosphonic acids and preparation of phosphahomocysteines of high enantiomeric excess
Qian, Renzhe,Horak, Jeannie,Hammerschmidt, Friedrich
, p. 737 - 744 (2017/06/05)
A variety of nitriles was reduced to diisobutylaluminum salts of aldimines, to which diisopropyl phosphite was added. The corresponding 1-aminophosphonates were either deprotected to give racemic 1-aminophosphonic acids or reacted with Boc2O to yield N-Boc-protected 1-aminophosphonates. The enantiomers of 2-benzylthio-1-(t-butoxycarbonylamino)propylphosphonate were obtained from the racemate by chiral HPLC and converted to phosphonic acid analogs of (R)- and (S)-homocysteine, (R)- and (S)-2-aminobutyric acid and (S)-methionine, all of ee >97% as determined by chiral HPLC.
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.
A versatile asymmetric synthesis of α-amino α-alkyl-phosphonic acids of high enantiomeric purity
Hanessian, Stephen,Bennani, Youssef L.
, p. 6465 - 6468 (2007/10/02)
A general protocol for the synthesis of α-amino-α- alkyl phosphonic acids in either enantiomeric form is described based on the alkylation of chiral bicyclic phosphonamides derived from (R,R)- and (S,S)-1,2-diaminocyclohexane.