Synthesis of β‑Hydroxy α‑Amino Acids Through Brønsted 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 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 frame...

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Bibliographic Details
Published in:Journal of organic chemistry 2021-06, Vol.86 (11), p.7757-7772
Main Authors: Vera, Silvia, Vázquez, Ana, Rodriguez, Ricardo, del Pozo, Sandra, Urruzuno, Iñaki, de Cózar, Abel, Mielgo, Antonia, Palomo, Claudio
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c00406