Cargando…
Tosylhydrazine-promoted self-conjugate reduction–Michael/aldol reaction of 3-phenacylideneoxindoles towards dispirocyclopentanebisoxindole derivatives
An efficient tosylhydrazine-mediated conjugate reduction of 3-phenacylideneoxindole and sequential Michael/intramolecular aldol reaction is reported under base-catalyzed conditions towards the formation of densely substituted dispirocyclopentanebisoxindole derivatives. The reaction proceeded in a di...
| Autores principales: | , |
|---|---|
| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
Beilstein-Institut
2022
|
| Materias: | |
| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9062653/ https://www.ncbi.nlm.nih.gov/pubmed/35558650 http://dx.doi.org/10.3762/bjoc.18.49 |
| _version_ | 1784698993767350272 |
|---|---|
| author | Pramanik, Sayan Mukhopadhyay, Chhanda |
| author_facet | Pramanik, Sayan Mukhopadhyay, Chhanda |
| author_sort | Pramanik, Sayan |
| collection | PubMed |
| description | An efficient tosylhydrazine-mediated conjugate reduction of 3-phenacylideneoxindole and sequential Michael/intramolecular aldol reaction is reported under base-catalyzed conditions towards the formation of densely substituted dispirocyclopentanebisoxindole derivatives. The reaction proceeded in a diastereoselective manner to afford four chiral stereocenters. The method also has advantages of wide substrate scope, readily available starting materials and operational simplicity through one pot reaction. |
| format | Online Article Text |
| id | pubmed-9062653 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2022 |
| publisher | Beilstein-Institut |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-90626532022-05-11 Tosylhydrazine-promoted self-conjugate reduction–Michael/aldol reaction of 3-phenacylideneoxindoles towards dispirocyclopentanebisoxindole derivatives Pramanik, Sayan Mukhopadhyay, Chhanda Beilstein J Org Chem Full Research Paper An efficient tosylhydrazine-mediated conjugate reduction of 3-phenacylideneoxindole and sequential Michael/intramolecular aldol reaction is reported under base-catalyzed conditions towards the formation of densely substituted dispirocyclopentanebisoxindole derivatives. The reaction proceeded in a diastereoselective manner to afford four chiral stereocenters. The method also has advantages of wide substrate scope, readily available starting materials and operational simplicity through one pot reaction. Beilstein-Institut 2022-04-27 /pmc/articles/PMC9062653/ /pubmed/35558650 http://dx.doi.org/10.3762/bjoc.18.49 Text en Copyright © 2022, Pramanik and Mukhopadhyay 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 | Full Research Paper Pramanik, Sayan Mukhopadhyay, Chhanda Tosylhydrazine-promoted self-conjugate reduction–Michael/aldol reaction of 3-phenacylideneoxindoles towards dispirocyclopentanebisoxindole derivatives |
| title | Tosylhydrazine-promoted self-conjugate reduction–Michael/aldol reaction of 3-phenacylideneoxindoles towards dispirocyclopentanebisoxindole derivatives |
| title_full | Tosylhydrazine-promoted self-conjugate reduction–Michael/aldol reaction of 3-phenacylideneoxindoles towards dispirocyclopentanebisoxindole derivatives |
| title_fullStr | Tosylhydrazine-promoted self-conjugate reduction–Michael/aldol reaction of 3-phenacylideneoxindoles towards dispirocyclopentanebisoxindole derivatives |
| title_full_unstemmed | Tosylhydrazine-promoted self-conjugate reduction–Michael/aldol reaction of 3-phenacylideneoxindoles towards dispirocyclopentanebisoxindole derivatives |
| title_short | Tosylhydrazine-promoted self-conjugate reduction–Michael/aldol reaction of 3-phenacylideneoxindoles towards dispirocyclopentanebisoxindole derivatives |
| title_sort | tosylhydrazine-promoted self-conjugate reduction–michael/aldol reaction of 3-phenacylideneoxindoles towards dispirocyclopentanebisoxindole derivatives |
| topic | Full Research Paper |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9062653/ https://www.ncbi.nlm.nih.gov/pubmed/35558650 http://dx.doi.org/10.3762/bjoc.18.49 |
| work_keys_str_mv | AT pramaniksayan tosylhydrazinepromotedselfconjugatereductionmichaelaldolreactionof3phenacylideneoxindolestowardsdispirocyclopentanebisoxindolederivatives AT mukhopadhyaychhanda tosylhydrazinepromotedselfconjugatereductionmichaelaldolreactionof3phenacylideneoxindolestowardsdispirocyclopentanebisoxindolederivatives |