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Highly regioselective synthesis of lactams via cascade reaction of α,β-unsaturated ketones, ketoamides, and DBU as a catalyst
Herein, the aldol/Michael cascade reaction on the β,γ-positions of α,β-unsaturated ketones with ketoamides to construct bicyclic lactams via DBU catalysis has been developed. The substrates were well-tolerated with high regio- and diastereoselectivities in moderate to good yields (32 examples). The...
| Autores principales: | , , , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
The Royal Society of Chemistry
2023
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| Materias: | |
| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9901288/ https://www.ncbi.nlm.nih.gov/pubmed/36760281 http://dx.doi.org/10.1039/d2ra07117g |
| _version_ | 1784883002627588096 |
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| author | Qin, Xin Zhang, Jinhai Wang, Zhan-Yong Song, Yimei Yang, Yixiao Zhang, Wenhai Liu, Hongxin |
| author_facet | Qin, Xin Zhang, Jinhai Wang, Zhan-Yong Song, Yimei Yang, Yixiao Zhang, Wenhai Liu, Hongxin |
| author_sort | Qin, Xin |
| collection | PubMed |
| description | Herein, the aldol/Michael cascade reaction on the β,γ-positions of α,β-unsaturated ketones with ketoamides to construct bicyclic lactams via DBU catalysis has been developed. The substrates were well-tolerated with high regio- and diastereoselectivities in moderate to good yields (32 examples). The control experiments revealed that the hydrogen of the amide was the key factor. |
| format | Online Article Text |
| id | pubmed-9901288 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2023 |
| publisher | The Royal Society of Chemistry |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-99012882023-02-08 Highly regioselective synthesis of lactams via cascade reaction of α,β-unsaturated ketones, ketoamides, and DBU as a catalyst Qin, Xin Zhang, Jinhai Wang, Zhan-Yong Song, Yimei Yang, Yixiao Zhang, Wenhai Liu, Hongxin RSC Adv Chemistry Herein, the aldol/Michael cascade reaction on the β,γ-positions of α,β-unsaturated ketones with ketoamides to construct bicyclic lactams via DBU catalysis has been developed. The substrates were well-tolerated with high regio- and diastereoselectivities in moderate to good yields (32 examples). The control experiments revealed that the hydrogen of the amide was the key factor. The Royal Society of Chemistry 2023-02-06 /pmc/articles/PMC9901288/ /pubmed/36760281 http://dx.doi.org/10.1039/d2ra07117g Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/ |
| spellingShingle | Chemistry Qin, Xin Zhang, Jinhai Wang, Zhan-Yong Song, Yimei Yang, Yixiao Zhang, Wenhai Liu, Hongxin Highly regioselective synthesis of lactams via cascade reaction of α,β-unsaturated ketones, ketoamides, and DBU as a catalyst |
| title | Highly regioselective synthesis of lactams via cascade reaction of α,β-unsaturated ketones, ketoamides, and DBU as a catalyst |
| title_full | Highly regioselective synthesis of lactams via cascade reaction of α,β-unsaturated ketones, ketoamides, and DBU as a catalyst |
| title_fullStr | Highly regioselective synthesis of lactams via cascade reaction of α,β-unsaturated ketones, ketoamides, and DBU as a catalyst |
| title_full_unstemmed | Highly regioselective synthesis of lactams via cascade reaction of α,β-unsaturated ketones, ketoamides, and DBU as a catalyst |
| title_short | Highly regioselective synthesis of lactams via cascade reaction of α,β-unsaturated ketones, ketoamides, and DBU as a catalyst |
| title_sort | highly regioselective synthesis of lactams via cascade reaction of α,β-unsaturated ketones, ketoamides, and dbu as a catalyst |
| topic | Chemistry |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9901288/ https://www.ncbi.nlm.nih.gov/pubmed/36760281 http://dx.doi.org/10.1039/d2ra07117g |
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