Conversion of nitriles to 1-aminophosphonic acids and preparation of phosphahomocysteines of high enantiomeric excess
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS(2017)
摘要
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 Boc(2)O 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.
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关键词
Nitriles,1-aminophosphonic acids,phosphahomocysteine,desulfurization,enantiomeric excess,chiral HPLC,6-aminoquinolyl-N-hydroxysuccinimidyl carbamate
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