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Chiral donor–acceptor azetines as powerful reactants for synthesis of amino acid derivatives
Coupling reactions of amines and alcohols are of central importance for applications in chemistry and biology. These transformations typically involve the use of a reagent, activated as an electrophile, onto which nucleophile coupling results in the formation of a carbon-nitrogen or a carbon–oxygen...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Nature Publishing Group UK
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6874555/ https://www.ncbi.nlm.nih.gov/pubmed/31757976 http://dx.doi.org/10.1038/s41467-019-13326-8 |
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author | Marichev, Kostiantyn O. Dong, Kuiyong Massey, Lynée A. Deng, Yongming De Angelis, Luca Wang, Kan Arman, Hadi Doyle, Michael P. |
author_facet | Marichev, Kostiantyn O. Dong, Kuiyong Massey, Lynée A. Deng, Yongming De Angelis, Luca Wang, Kan Arman, Hadi Doyle, Michael P. |
author_sort | Marichev, Kostiantyn O. |
collection | PubMed |
description | Coupling reactions of amines and alcohols are of central importance for applications in chemistry and biology. These transformations typically involve the use of a reagent, activated as an electrophile, onto which nucleophile coupling results in the formation of a carbon-nitrogen or a carbon–oxygen bond. Several promising reagents and procedures have been developed to achieve these bond forming processes in high yields with excellent stereocontrol, but few offer direct coupling without the intervention of a catalyst. Herein, we report the synthesis of chiral donor–acceptor azetines by highly enantioselective [3 + 1]-cycloaddition of enoldiazoacetates with aza-ylides and their selective coupling with nitrogen and oxygen nucleophiles via 3-azetidinones to form amino acid derivatives, including those of peptides and natural products. The overall process is general for a broad spectrum of nucleophiles, has a high degree of electronic and steric selectivity, and retains the enantiopurity of the original azetine. |
format | Online Article Text |
id | pubmed-6874555 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
spelling | pubmed-68745552019-11-25 Chiral donor–acceptor azetines as powerful reactants for synthesis of amino acid derivatives Marichev, Kostiantyn O. Dong, Kuiyong Massey, Lynée A. Deng, Yongming De Angelis, Luca Wang, Kan Arman, Hadi Doyle, Michael P. Nat Commun Article Coupling reactions of amines and alcohols are of central importance for applications in chemistry and biology. These transformations typically involve the use of a reagent, activated as an electrophile, onto which nucleophile coupling results in the formation of a carbon-nitrogen or a carbon–oxygen bond. Several promising reagents and procedures have been developed to achieve these bond forming processes in high yields with excellent stereocontrol, but few offer direct coupling without the intervention of a catalyst. Herein, we report the synthesis of chiral donor–acceptor azetines by highly enantioselective [3 + 1]-cycloaddition of enoldiazoacetates with aza-ylides and their selective coupling with nitrogen and oxygen nucleophiles via 3-azetidinones to form amino acid derivatives, including those of peptides and natural products. The overall process is general for a broad spectrum of nucleophiles, has a high degree of electronic and steric selectivity, and retains the enantiopurity of the original azetine. Nature Publishing Group UK 2019-11-22 /pmc/articles/PMC6874555/ /pubmed/31757976 http://dx.doi.org/10.1038/s41467-019-13326-8 Text en © The Author(s) 2019 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/. |
spellingShingle | Article Marichev, Kostiantyn O. Dong, Kuiyong Massey, Lynée A. Deng, Yongming De Angelis, Luca Wang, Kan Arman, Hadi Doyle, Michael P. Chiral donor–acceptor azetines as powerful reactants for synthesis of amino acid derivatives |
title | Chiral donor–acceptor azetines as powerful reactants for synthesis of amino acid derivatives |
title_full | Chiral donor–acceptor azetines as powerful reactants for synthesis of amino acid derivatives |
title_fullStr | Chiral donor–acceptor azetines as powerful reactants for synthesis of amino acid derivatives |
title_full_unstemmed | Chiral donor–acceptor azetines as powerful reactants for synthesis of amino acid derivatives |
title_short | Chiral donor–acceptor azetines as powerful reactants for synthesis of amino acid derivatives |
title_sort | chiral donor–acceptor azetines as powerful reactants for synthesis of amino acid derivatives |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6874555/ https://www.ncbi.nlm.nih.gov/pubmed/31757976 http://dx.doi.org/10.1038/s41467-019-13326-8 |
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