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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...

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Autores principales: Rainoldi, Giulia, Faltracco, Matteo, Spatti, Claudia, Silvani, Alessandra, Lesma, Giordano
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
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.
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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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