Synthesis of β-Hydroxy α-Amino Acids Through Brønsted Base-Catalyzed syn-Selective Direct Aldol Reaction of Schiff Bases of Glycine o-Nitroanilide
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Date
2021-05-16Author
Vera Salas, Silvia
Vázquez, Ana
Rodríguez Urretavizcaya, Ricardo
Del Pozo, Sandra
Urruzuno Guiu, Iñaki
De Cózar Ruano, Abel
Palomo Nicolau, Claudio
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Journal of Organic Chemistry 86(11) : 7757-7772 (2021)
Abstract
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.