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Organocatalytic Access to Enantioenriched Spirooxindole-Based 4-Methyleneazetidines
This work describes the synthesis of enantioenriched spiro compounds, incorporating the azetidine and the oxindole motifs. The preparation relies on a formal [2 + 2] annulation reaction of isatin-derived N-tert-butylsulfonyl ketimines with allenoates. The asymmetric induction is secured by an organo...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6150293/ https://www.ncbi.nlm.nih.gov/pubmed/29160827 http://dx.doi.org/10.3390/molecules22112016 |
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author | Rainoldi, Giulia Faltracco, Matteo Spatti, Claudia Silvani, Alessandra Lesma, Giordano |
author_facet | Rainoldi, Giulia Faltracco, Matteo Spatti, Claudia Silvani, Alessandra Lesma, Giordano |
author_sort | Rainoldi, Giulia |
collection | PubMed |
description | This work describes the synthesis of enantioenriched spiro compounds, incorporating the azetidine and the oxindole motifs. The preparation relies on a formal [2 + 2] annulation reaction of isatin-derived N-tert-butylsulfonyl ketimines with allenoates. The asymmetric induction is secured by an organocatalytic strategy, exploiting a bifunctional cinchona-type β-isocupridine-based catalyst. Some post-transformation products, including unexpected spiropyrroline and 3,3-disubstituted oxindole derivatives, are also presented. |
format | Online Article Text |
id | pubmed-6150293 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-61502932018-11-13 Organocatalytic Access to Enantioenriched Spirooxindole-Based 4-Methyleneazetidines Rainoldi, Giulia Faltracco, Matteo Spatti, Claudia Silvani, Alessandra Lesma, Giordano Molecules Article This work describes the synthesis of enantioenriched spiro compounds, incorporating the azetidine and the oxindole motifs. The preparation relies on a formal [2 + 2] annulation reaction of isatin-derived N-tert-butylsulfonyl ketimines with allenoates. The asymmetric induction is secured by an organocatalytic strategy, exploiting a bifunctional cinchona-type β-isocupridine-based catalyst. Some post-transformation products, including unexpected spiropyrroline and 3,3-disubstituted oxindole derivatives, are also presented. MDPI 2017-11-21 /pmc/articles/PMC6150293/ /pubmed/29160827 http://dx.doi.org/10.3390/molecules22112016 Text en © 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Rainoldi, Giulia Faltracco, Matteo Spatti, Claudia Silvani, Alessandra Lesma, Giordano Organocatalytic Access to Enantioenriched Spirooxindole-Based 4-Methyleneazetidines |
title | Organocatalytic Access to Enantioenriched Spirooxindole-Based 4-Methyleneazetidines |
title_full | Organocatalytic Access to Enantioenriched Spirooxindole-Based 4-Methyleneazetidines |
title_fullStr | Organocatalytic Access to Enantioenriched Spirooxindole-Based 4-Methyleneazetidines |
title_full_unstemmed | Organocatalytic Access to Enantioenriched Spirooxindole-Based 4-Methyleneazetidines |
title_short | Organocatalytic Access to Enantioenriched Spirooxindole-Based 4-Methyleneazetidines |
title_sort | organocatalytic access to enantioenriched spirooxindole-based 4-methyleneazetidines |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6150293/ https://www.ncbi.nlm.nih.gov/pubmed/29160827 http://dx.doi.org/10.3390/molecules22112016 |
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