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-diaminophosphonates by conventional reductive processes.
A new and expedient diastereoselective synthesis of alpha-(hydroxyamino)phosphonates and alpha-aminophosphonates by silyl triflate promoted diethyl phosphite addition to chiral N-benzyl nitrones
DE RISI, Carmela;PERRONE, Daniela;DONDONI, Alessandro;POLLINI, Gian Piero;BERTOLASI, Valerio
2003
Abstract
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-diaminophosphonates by conventional reductive processes.File in questo prodotto:
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