O-silyl triflate-promoted addition of diethyl phosphite to chiral aldonitrones.: A rapid access to complex α-amino phosphonates and their N-hydroxy derivatives

The addition reaction of diethyl phosphite to O-silylated N-benzyl nitrones derived from chiral alpha -alkoxy and N-Boc alpha -amino aldehydes has been studied as a stereoselective carbon-phosphorus bond forming process for the synthesis of polyhydroxylated alpha -amino and alpha,beta -diamino phosphonates. Key intermediates are the corresponding N-hydroxy alpha -amino phosphonates. (C) 2001 Elsevier Science Ltd. All rights reserved.