Preparation of phosphinodipeptide analogs as building blocks for pseudopeptides synthesis

A simple and effective preparation of phosphinodipeptides, in good overall yields, has been developed, This one pot procedure, allowing the variation of the substituents in alpha and/or beta position to the phosphorus atom and also in alpha position to the nitrogen atom, consists in the addition of alkyl hypophosphites to imines. followed by Michael-addition on acrylates. To show the value of phosphinodipeptides analogs I as synthetic intermediates, selective deprotections of the three functional groups are described. (C) 2002 Elsevier Science B.V. All rights reserved.