98049-00-4Relevant 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.
A simple and general method for the asymmetric synthesis of α-aminophosphonic acids
Maury,Royer,Husson
, p. 6127 - 6130 (2007/10/02)
A simple and general method for the asymmetric synthesis of α-aminophosphonic acids is described. A chiral phosphonate prepared in one step from R-(-)-phenylglycinol was alkylated with good diastereoselectivity using different electrophiles.