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

[Image: see text] 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-...

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Detalles Bibliográficos
Autores principales: Vera, Silvia, Vázquez, Ana, Rodriguez, Ricardo, del Pozo, Sandra, Urruzuno, Iñaki, de Cózar, Abel, Mielgo, Antonia, Palomo, Claudio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9490875/
https://www.ncbi.nlm.nih.gov/pubmed/33998227
http://dx.doi.org/10.1021/acs.joc.1c00406
Descripción
Sumario:[Image: see text] 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.