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Decarboxylative 1,3-dipolar cycloaddition of amino acids for the synthesis of heterocyclic compounds

The [3 + 2] cycloadditions of stabilized azomethine ylides (AMYs) derived from amino esters are well-established. However, the reactions of semi-stabilized AMYs generated from decarboxylative condensation of α-amino acids with arylaldehydes are much less explored. The [3 + 2] adducts of α-amino acid...

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Autores principales: Zhang, Xiaofeng, Ma, Xiaoming, Zhang, Wei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10644012/
https://www.ncbi.nlm.nih.gov/pubmed/38025085
http://dx.doi.org/10.3762/bjoc.19.123
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author Zhang, Xiaofeng
Ma, Xiaoming
Zhang, Wei
author_facet Zhang, Xiaofeng
Ma, Xiaoming
Zhang, Wei
author_sort Zhang, Xiaofeng
collection PubMed
description The [3 + 2] cycloadditions of stabilized azomethine ylides (AMYs) derived from amino esters are well-established. However, the reactions of semi-stabilized AMYs generated from decarboxylative condensation of α-amino acids with arylaldehydes are much less explored. The [3 + 2] adducts of α-amino acids could be used for a second [3 + 2] cycloaddition as well as for other post-condensation modifications. This article highlights our recent work on the development of α-amino acid-based [3 + 2] cycloaddition reactions of N–H-type AMYs in multicomponent, one-pot, and stepwise reactions for the synthesis of diverse heterocycles related to some bioactive compounds and natural products.
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spelling pubmed-106440122023-11-06 Decarboxylative 1,3-dipolar cycloaddition of amino acids for the synthesis of heterocyclic compounds Zhang, Xiaofeng Ma, Xiaoming Zhang, Wei Beilstein J Org Chem Commentary The [3 + 2] cycloadditions of stabilized azomethine ylides (AMYs) derived from amino esters are well-established. However, the reactions of semi-stabilized AMYs generated from decarboxylative condensation of α-amino acids with arylaldehydes are much less explored. The [3 + 2] adducts of α-amino acids could be used for a second [3 + 2] cycloaddition as well as for other post-condensation modifications. This article highlights our recent work on the development of α-amino acid-based [3 + 2] cycloaddition reactions of N–H-type AMYs in multicomponent, one-pot, and stepwise reactions for the synthesis of diverse heterocycles related to some bioactive compounds and natural products. Beilstein-Institut 2023-11-06 /pmc/articles/PMC10644012/ /pubmed/38025085 http://dx.doi.org/10.3762/bjoc.19.123 Text en Copyright © 2023, Zhang et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Commentary
Zhang, Xiaofeng
Ma, Xiaoming
Zhang, Wei
Decarboxylative 1,3-dipolar cycloaddition of amino acids for the synthesis of heterocyclic compounds
title Decarboxylative 1,3-dipolar cycloaddition of amino acids for the synthesis of heterocyclic compounds
title_full Decarboxylative 1,3-dipolar cycloaddition of amino acids for the synthesis of heterocyclic compounds
title_fullStr Decarboxylative 1,3-dipolar cycloaddition of amino acids for the synthesis of heterocyclic compounds
title_full_unstemmed Decarboxylative 1,3-dipolar cycloaddition of amino acids for the synthesis of heterocyclic compounds
title_short Decarboxylative 1,3-dipolar cycloaddition of amino acids for the synthesis of heterocyclic compounds
title_sort decarboxylative 1,3-dipolar cycloaddition of amino acids for the synthesis of heterocyclic compounds
topic Commentary
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10644012/
https://www.ncbi.nlm.nih.gov/pubmed/38025085
http://dx.doi.org/10.3762/bjoc.19.123
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