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

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)