Synthesis of β-Hydroxy α-Amino Acids Through Brønsted Base-Catalyzed syn-Selective Direct Aldol Reaction of Schiff Bases of Glycine o-Nitroanilide
Ikusi/ Ireki
Data
2021-05-16Egilea
Vera Salas, Silvia
Vázquez, Ana
Rodríguez Urretavizcaya, Ricardo
Del Pozo, Sandra
Urruzuno Guiu, Iñaki
De Cózar Ruano, Abel
Palomo Nicolau, Claudio
Journal of Organic Chemistry 86(11) : 7757-7772 (2021)
Laburpena
Here we report the highly enantio- and syn-selective synthesis of β-hydroxy α-amino acids from glycine imine derivatives under Brønsted 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.