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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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
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author Vera, Silvia
Vázquez, Ana
Rodriguez, Ricardo
del Pozo, Sandra
Urruzuno, Iñaki
de Cózar, Abel
Mielgo, Antonia
Palomo, Claudio
author_facet Vera, Silvia
Vázquez, Ana
Rodriguez, Ricardo
del Pozo, Sandra
Urruzuno, Iñaki
de Cózar, Abel
Mielgo, Antonia
Palomo, Claudio
author_sort Vera, Silvia
collection PubMed
description [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.
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spelling pubmed-94908752022-09-22 Synthesis of β-Hydroxy α-Amino Acids Through Brønsted Base-Catalyzed syn-Selective Direct Aldol Reaction of Schiff Bases of Glycine o-Nitroanilide Vera, Silvia Vázquez, Ana Rodriguez, Ricardo del Pozo, Sandra Urruzuno, Iñaki de Cózar, Abel Mielgo, Antonia Palomo, Claudio J Org Chem [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. American Chemical Society 2021-05-16 2021-06-04 /pmc/articles/PMC9490875/ /pubmed/33998227 http://dx.doi.org/10.1021/acs.joc.1c00406 Text en © 2021 American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Vera, Silvia
Vázquez, Ana
Rodriguez, Ricardo
del Pozo, Sandra
Urruzuno, Iñaki
de Cózar, Abel
Mielgo, Antonia
Palomo, Claudio
Synthesis of β-Hydroxy α-Amino Acids Through Brønsted Base-Catalyzed syn-Selective Direct Aldol Reaction of Schiff Bases of Glycine o-Nitroanilide
title Synthesis of β-Hydroxy α-Amino Acids Through Brønsted Base-Catalyzed syn-Selective Direct Aldol Reaction of Schiff Bases of Glycine o-Nitroanilide
title_full Synthesis of β-Hydroxy α-Amino Acids Through Brønsted Base-Catalyzed syn-Selective Direct Aldol Reaction of Schiff Bases of Glycine o-Nitroanilide
title_fullStr Synthesis of β-Hydroxy α-Amino Acids Through Brønsted Base-Catalyzed syn-Selective Direct Aldol Reaction of Schiff Bases of Glycine o-Nitroanilide
title_full_unstemmed Synthesis of β-Hydroxy α-Amino Acids Through Brønsted Base-Catalyzed syn-Selective Direct Aldol Reaction of Schiff Bases of Glycine o-Nitroanilide
title_short Synthesis of β-Hydroxy α-Amino Acids Through Brønsted Base-Catalyzed syn-Selective Direct Aldol Reaction of Schiff Bases of Glycine o-Nitroanilide
title_sort synthesis of β-hydroxy α-amino acids through brønsted base-catalyzed syn-selective direct aldol reaction of schiff bases of glycine o-nitroanilide
url 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
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