Synthesis Of Beta-Hydroxy Alpha-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.