Diastereoselective nucleophilic addition of acetylide to N-benzyl-2, 3- O-isopropylidene-D-glyceraldehyde nitrone (BIGN). Stereodivergent synthesis of β-hydroxy-α-(hydroxyamino)- and βhydroxy-α-amino acids

Article abstract of DOI:10.1016/S0957-4166(97)00438-2

The stereocontrolled nucleophilic addition of lithium trimethylsilyl acetylide to the N-benzyl nitrone (BIGN) derived from 2,3-O-isopropylidene- D-glyceraldehyde, followed by oxidative cleavage of the ensuing propargyl hydroxylamines resulted in an efficient stereodivergent synthesis of fully protected epimeric N. hydroxy α-amino esters 8 and 13 as well as the corresponding α-amino esters 9 and 14.