Synthesis of Phosphoramides for the Lewis Base-Catalyzed Allylation and Aldol Addition Reactions

J Org Chem. 1999 Mar 19;64(6):1958-1967. doi: 10.1021/jo9820723.


Both chiral and achiral phosphoramides of diverse structure were prepared from diamines by the coupling to phosphorus(V) or phosphorus(III) reagents. Several enantiopure 1,2-diphenyl-1,2-ethanediamine analogues have been prepared by the reductive coupling of the corresponding N-silylimine with NbCl(4)(THF)(2) and subsequent resolution by the formation of diastereomeric menthyl carbamates. (S,S)-N,N'-Di-(1-naphthyl)-1,2-diphenyl-1,2-ethanediamine 15 was prepared by the arylation of (S,S)-1,2-diphenyl-1,2-ethanediamine with naphthyl iodide.