Stereocontrolled synthesis of pseudo C2-symmetric 1,3-diamino-2-propanol core units of HIV protease inhibitors

Article abstract of DOI:10.1016/S0040-4039(96)02355-6

The synthesis of the pseudo C₂-symmetric dibenzyldiamino alcohol (S,S)-1 and the two meso stereoisomers 1a and 1b (R = PhCH₂) is described by stereocontrolled benzylmagnesium chloride addition to the nitrones 3 derived from chiral β-amino-α-hydroxy aldehydes 2 that in turn were obtained from phenylalanino; the overall yield of (S,S)-1 is 23% from N-Boc L-phenylalaninal; the antipode (R,R)-1 can be prepared in a similar way starting from the D-isomer of the same α-amino aldehyde.