Post-Ugi gold-catalyzed diastereoselective domino cyclization for the synthesis of diversely substituted spiroindolines
An Ugi four-component reaction of propargylamine with 3-formylindole and various acids and isonitriles produces adducts which are subjected to a cationic gold-catalyzed diastereoselective domino cyclization to furnish diversely substituted spiroindolines. All the reactions run via an exo-dig attack...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2013-10-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.9.246 |
| _version_ | 1818912587543216128 |
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| author | Amit Kumar Dipak D. Vachhani Sachin G. Modha Sunil K. Sharma Virinder S. Parmar Erik V. Van der Eycken |
| author_facet | Amit Kumar Dipak D. Vachhani Sachin G. Modha Sunil K. Sharma Virinder S. Parmar Erik V. Van der Eycken |
| author_sort | Amit Kumar |
| collection | DOAJ |
| description | An Ugi four-component reaction of propargylamine with 3-formylindole and various acids and isonitriles produces adducts which are subjected to a cationic gold-catalyzed diastereoselective domino cyclization to furnish diversely substituted spiroindolines. All the reactions run via an exo-dig attack in the hydroarylation step followed by an intramolecular diastereoselective trapping of the imminium ion. The whole sequence is atom economic and the application of a multicomponent reaction assures diversity. |
| first_indexed | 2024-12-19T23:16:58Z |
| format | Article |
| id | doaj.art-4a008db97b804404a9f6914e64276ca3 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-19T23:16:58Z |
| publishDate | 2013-10-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-4a008db97b804404a9f6914e64276ca32022-12-21T20:02:04ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972013-10-01912097210210.3762/bjoc.9.2461860-5397-9-246Post-Ugi gold-catalyzed diastereoselective domino cyclization for the synthesis of diversely substituted spiroindolinesAmit Kumar0Dipak D. Vachhani1Sachin G. Modha2Sunil K. Sharma3Virinder S. Parmar4Erik V. Van der Eycken5Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, 3001, Leuven, BelgiumLaboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, 3001, Leuven, BelgiumLaboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, 3001, Leuven, BelgiumBioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi-110 007, IndiaBioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi-110 007, IndiaLaboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, 3001, Leuven, BelgiumAn Ugi four-component reaction of propargylamine with 3-formylindole and various acids and isonitriles produces adducts which are subjected to a cationic gold-catalyzed diastereoselective domino cyclization to furnish diversely substituted spiroindolines. All the reactions run via an exo-dig attack in the hydroarylation step followed by an intramolecular diastereoselective trapping of the imminium ion. The whole sequence is atom economic and the application of a multicomponent reaction assures diversity.https://doi.org/10.3762/bjoc.9.246alkynesgoldindolesmulticomponentspiroindolinesUgi |
| spellingShingle | Amit Kumar Dipak D. Vachhani Sachin G. Modha Sunil K. Sharma Virinder S. Parmar Erik V. Van der Eycken Post-Ugi gold-catalyzed diastereoselective domino cyclization for the synthesis of diversely substituted spiroindolines Beilstein Journal of Organic Chemistry alkynes gold indoles multicomponent spiroindolines Ugi |
| title | Post-Ugi gold-catalyzed diastereoselective domino cyclization for the synthesis of diversely substituted spiroindolines |
| title_full | Post-Ugi gold-catalyzed diastereoselective domino cyclization for the synthesis of diversely substituted spiroindolines |
| title_fullStr | Post-Ugi gold-catalyzed diastereoselective domino cyclization for the synthesis of diversely substituted spiroindolines |
| title_full_unstemmed | Post-Ugi gold-catalyzed diastereoselective domino cyclization for the synthesis of diversely substituted spiroindolines |
| title_short | Post-Ugi gold-catalyzed diastereoselective domino cyclization for the synthesis of diversely substituted spiroindolines |
| title_sort | post ugi gold catalyzed diastereoselective domino cyclization for the synthesis of diversely substituted spiroindolines |
| topic | alkynes gold indoles multicomponent spiroindolines Ugi |
| url | https://doi.org/10.3762/bjoc.9.246 |
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