A facile transformation of the δ-hydroxy-α-amino lactones from α- furfuryl amide

Article abstract of DOI:10.1016/S0040-4020(98)00736-4

(S)- and (R)- α- furfuryl amides, obtained from the kinetic resolution of (R, S)- α- furfuryl amide using the modified Sharpless asymmetric epoxidation, have been transformed into four 8-hydroxy α- amino lactones (1S, 3S)-1, (1R, 3R)-1, (1S, 3R)-1, (1R, 3S)-1, using sharpless asymmetric dihydroxylation as the key step. The much more efficient method of the addition of chiral aldimine 10 with allylic Grignard reagent for preparation of (S, S)-1 was also achieved.