Synthesis of β-Hydroxy α-Amino Acids Through Bronsted Base-Catalyzed syn-Selective Direct Aldol Reaction of Schiff Bases of Glycine o-Nitroanilide

Here we report the highly enantio- and syn-selective synthesis of beta-hydroxy alpha-amino acids from glycine imine derivatives under Bronsted base (BB) catalysis. The key of this approach is the use of benzophenone-derived imine of glycine o-nitroanilide as a pronucleophile, where the o-nitroanilide framework provides an efficient hydrogen-bonding platform that accounts for nucleophile reactivity and diastereoselectivity.

Automated summary

This study reports a highly enantio- and syn-selective synthesis of beta-hydroxy alpha-amino acids from glycine imine derivatives under Bronsted base catalysis. The key lies in the use of benzophenone-derived imine of glycine o-nitroanilide as a pronucleophile, where the o-nitroanilide framework provides an efficient hydrogen-bonding platform that accounts for nucleophile reactivity and diastereoselectivity.