A New and Expedient Diastereoselective Synthesis of α‐(Hydroxyamino)phosphonates and α‐Aminophosphonates by Silyl Triflate Promoted Diethyl Phosphite Addition to Chiral N‐Benzyl Nitrones.

Abstract

An efficient methodology for the synthesis of α-aminophosphonates has been developed taking advantage of the tert-butyldimethylsilyl triflate activated addition of diethyl phosphite to N-benzyl nitrones derived from chiral α-alkoxy and α-(Boc-amino) aldehydes. The stereoselective carbon− phosphorus bond-forming reaction proceeded smoothly to give α-(hydroxyamino)phosphonate intermediates as the primary adducts, which were subsequently converted into the corresponding polyhydroxylated α-amino- and α,β-diaminophosphonates by conventional reductive processes. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)