Asymmetric Ugi 3CR on isatin-derived ketimine: synthesis of chiral 3,3-disubstituted 3-aminooxindole derivatives

An efficient Ugi three-component reaction of a preformed chiral ketimine derived from isatin with various isonitrile and acid components has been developed. The reactions proceeded smoothly and in a stereocontrolled manner with regard to the new center of the Ugi products due to the stereoinduction...

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Autores principales: Lesma, Giordano, Meneghetti, Fiorella, Sacchetti, Alessandro, Stucchi, Mattia, Silvani, Alessandra
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077467/
https://www.ncbi.nlm.nih.gov/pubmed/24991292
http://dx.doi.org/10.3762/bjoc.10.141
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author Lesma, Giordano
Meneghetti, Fiorella
Sacchetti, Alessandro
Stucchi, Mattia
Silvani, Alessandra
author_facet Lesma, Giordano
Meneghetti, Fiorella
Sacchetti, Alessandro
Stucchi, Mattia
Silvani, Alessandra
author_sort Lesma, Giordano
collection PubMed
description An efficient Ugi three-component reaction of a preformed chiral ketimine derived from isatin with various isonitrile and acid components has been developed. The reactions proceeded smoothly and in a stereocontrolled manner with regard to the new center of the Ugi products due to the stereoinduction of the amine chiral residue. A wide variety of novel chiral 3,3-disubstituted 3-aminooxindoles were obtained, a selection of which were subjected to post-Ugi transformations, paving the way to application as peptidomimetics.
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spelling pubmed-40774672014-07-02 Asymmetric Ugi 3CR on isatin-derived ketimine: synthesis of chiral 3,3-disubstituted 3-aminooxindole derivatives Lesma, Giordano Meneghetti, Fiorella Sacchetti, Alessandro Stucchi, Mattia Silvani, Alessandra Beilstein J Org Chem Full Research Paper An efficient Ugi three-component reaction of a preformed chiral ketimine derived from isatin with various isonitrile and acid components has been developed. The reactions proceeded smoothly and in a stereocontrolled manner with regard to the new center of the Ugi products due to the stereoinduction of the amine chiral residue. A wide variety of novel chiral 3,3-disubstituted 3-aminooxindoles were obtained, a selection of which were subjected to post-Ugi transformations, paving the way to application as peptidomimetics. Beilstein-Institut 2014-06-18 /pmc/articles/PMC4077467/ /pubmed/24991292 http://dx.doi.org/10.3762/bjoc.10.141 Text en Copyright © 2014, Lesma 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
Lesma, Giordano
Meneghetti, Fiorella
Sacchetti, Alessandro
Stucchi, Mattia
Silvani, Alessandra
Asymmetric Ugi 3CR on isatin-derived ketimine: synthesis of chiral 3,3-disubstituted 3-aminooxindole derivatives
title Asymmetric Ugi 3CR on isatin-derived ketimine: synthesis of chiral 3,3-disubstituted 3-aminooxindole derivatives
title_full Asymmetric Ugi 3CR on isatin-derived ketimine: synthesis of chiral 3,3-disubstituted 3-aminooxindole derivatives
title_fullStr Asymmetric Ugi 3CR on isatin-derived ketimine: synthesis of chiral 3,3-disubstituted 3-aminooxindole derivatives
title_full_unstemmed Asymmetric Ugi 3CR on isatin-derived ketimine: synthesis of chiral 3,3-disubstituted 3-aminooxindole derivatives
title_short Asymmetric Ugi 3CR on isatin-derived ketimine: synthesis of chiral 3,3-disubstituted 3-aminooxindole derivatives
title_sort asymmetric ugi 3cr on isatin-derived ketimine: synthesis of chiral 3,3-disubstituted 3-aminooxindole derivatives
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077467/
https://www.ncbi.nlm.nih.gov/pubmed/24991292
http://dx.doi.org/10.3762/bjoc.10.141
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