Synthesis of enantiopure N-and C-protected homo-β-amino acids by direct homologation of α-amino acids

Article abstract of DOI:10.1016/0040-4020(95)00778-7

Enantiopure N-and/or C-protected homo-β-amino acids are prepared readily and in good yields from N-protected α-amino acids with the same side chain, via reduction of the carboxyl function and conversion of the resulting N-protected β-amino alcohol into the corresponding β-amino iodide and then β-amino cyanide. The key step of this strategy is represented by the synthesis of the enantiopure N-protected β-amino iodides 2 and 3 that are smoothly obtained from the parent amino alcohols 1 by polymer bound triarylphosphine-I₂ complex in anhydrous dichloromethane.