A New and Expedient Diastereoselective Synthesis of alpha-(Hydroxyamino)phosphonaates and alpha-Aminophosphonates by Silyl Triflate Promoted Diethyl Phosphite Addition to Chiral N-Benzyl Nitrones

摘要

An efficient methodology for the synthesis of alpha-aminophosphonates has been developed taking advantage of the tert-butyldimethylsilyl triflate activated addition of diethyl phosphite to N-benzyl nitrones derived from chiral alpha-alkoxy and alpha-(Boc-amino) aldehydes. The stereoselective carbon-phosphorus bond-forming reaction proceeded smoothly to give alpha-(hydroxyamino)phosphonate intermediates as the primary adducts, which were subsequently converted into the corresponding polyhydroxylated alpha-amino-and alpha,beta-diami-nophosphonates by conventional reductive processes.