127258-28-0Relevant 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)
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.
Enantioselective synthesis of optically active homoallylamines by allylboration of N-diisobutylaluminum imines
Watanabe, Katsuhiro,Kuroda, Shizue,Yokoi, Ayako,Ito, Koichi,Itsuno, Shinichi
, p. 103 - 107 (2007/10/03)
Diisobutylaluminum hydride (DIBAL-H) reduces nitriles to give N-diisobutylaluminum imines, which were asymmetrically allylated with chirally modified allylboron reagents. The corresponding chiral primary homoallylamines were obtained with up to 87% ee.