Cargando…
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...
| Autores principales: | , , , , , |
|---|---|
| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
Beilstein-Institut
2013
|
| Materias: | |
| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3817510/ https://www.ncbi.nlm.nih.gov/pubmed/24204421 http://dx.doi.org/10.3762/bjoc.9.246 |
| _version_ | 1782478084864212992 |
|---|---|
| author | Kumar, Amit Vachhani, Dipak D Modha, Sachin G Sharma, Sunil K Parmar, Virinder S Van der Eycken, Erik V |
| author_facet | Kumar, Amit Vachhani, Dipak D Modha, Sachin G Sharma, Sunil K Parmar, Virinder S Van der Eycken, Erik V |
| author_sort | Kumar, Amit |
| collection | PubMed |
| 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. |
| format | Online Article Text |
| id | pubmed-3817510 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2013 |
| publisher | Beilstein-Institut |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-38175102013-11-07 Post-Ugi gold-catalyzed diastereoselective domino cyclization for the synthesis of diversely substituted spiroindolines Kumar, Amit Vachhani, Dipak D Modha, Sachin G Sharma, Sunil K Parmar, Virinder S Van der Eycken, Erik V Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2013-10-14 /pmc/articles/PMC3817510/ /pubmed/24204421 http://dx.doi.org/10.3762/bjoc.9.246 Text en Copyright © 2013, Kumar et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms) |
| spellingShingle | Full Research Paper Kumar, Amit Vachhani, Dipak D Modha, Sachin G Sharma, Sunil K Parmar, Virinder S Van der Eycken, Erik V Post-Ugi gold-catalyzed diastereoselective domino cyclization for the synthesis of diversely substituted spiroindolines |
| 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 | Full Research Paper |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3817510/ https://www.ncbi.nlm.nih.gov/pubmed/24204421 http://dx.doi.org/10.3762/bjoc.9.246 |
| work_keys_str_mv | AT kumaramit postugigoldcatalyzeddiastereoselectivedominocyclizationforthesynthesisofdiverselysubstitutedspiroindolines AT vachhanidipakd postugigoldcatalyzeddiastereoselectivedominocyclizationforthesynthesisofdiverselysubstitutedspiroindolines AT modhasaching postugigoldcatalyzeddiastereoselectivedominocyclizationforthesynthesisofdiverselysubstitutedspiroindolines AT sharmasunilk postugigoldcatalyzeddiastereoselectivedominocyclizationforthesynthesisofdiverselysubstitutedspiroindolines AT parmarvirinders postugigoldcatalyzeddiastereoselectivedominocyclizationforthesynthesisofdiverselysubstitutedspiroindolines AT vandereyckenerikv postugigoldcatalyzeddiastereoselectivedominocyclizationforthesynthesisofdiverselysubstitutedspiroindolines |