A general method for the synthesis of enantiomerically pure β- substituted, β-amino acids through α-substituted succinic acid derivatives

Article abstract of DOI:10.1021/jo990756k

A general procedure for the synthesis of enantiopure β-substituted, β- amino acids is presented. Alkylation of the sodium enolates derived from chiral N-acyloxazolidinone imides 2 (R = Me, i-Pr, t-Bu, Ph, Bn) with tert- butyl bromoacetate afforded the 2-substituted succinate derivatives 3 in good yields (82-89%) and with high selectivity (≥ 93;7). Following hydrolysis, Curtius rearrangement of the resulting carboxylic acid provided the enantiopure benzyloxycarbonyl (Cbz)-protected β-amino esters 6 in good yields (74-79%).