A Diastereoselective Synthesis of Dispiro[oxindole-cyclohexanone]pyrrolidines by 1,3-Dipolar Cycloaddition

For the first time, arylmethylidene cyclohexanones that are non-symmetrical due to the presence of peripheral substituents were studied in 1,3-dipolar cycloaddition reactions. It is shown that the interaction with the azomethine ylide generated from sarcosine proceeds regio- and diastereoselectively...

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Autores principales: Anis’kov, Alexander, Klochkova, Irina, Tumskiy, Roman, Yegorova, Alevtina
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6149807/
https://www.ncbi.nlm.nih.gov/pubmed/29207519
http://dx.doi.org/10.3390/molecules22122134
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author Anis’kov, Alexander
Klochkova, Irina
Tumskiy, Roman
Yegorova, Alevtina
author_facet Anis’kov, Alexander
Klochkova, Irina
Tumskiy, Roman
Yegorova, Alevtina
author_sort Anis’kov, Alexander
collection PubMed
description For the first time, arylmethylidene cyclohexanones that are non-symmetrical due to the presence of peripheral substituents were studied in 1,3-dipolar cycloaddition reactions. It is shown that the interaction with the azomethine ylide generated from sarcosine proceeds regio- and diastereoselectively, with the participation of two non-equivalent parts of the dipolarophile. Also for the first time, β-amino ketones (Mannich bases) were used as dipolarophile equivalents of unsaturated ketones. It was found that cycloaddition occurs diastereoselectively at the generated center.
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spelling pubmed-61498072018-11-13 A Diastereoselective Synthesis of Dispiro[oxindole-cyclohexanone]pyrrolidines by 1,3-Dipolar Cycloaddition Anis’kov, Alexander Klochkova, Irina Tumskiy, Roman Yegorova, Alevtina Molecules Article For the first time, arylmethylidene cyclohexanones that are non-symmetrical due to the presence of peripheral substituents were studied in 1,3-dipolar cycloaddition reactions. It is shown that the interaction with the azomethine ylide generated from sarcosine proceeds regio- and diastereoselectively, with the participation of two non-equivalent parts of the dipolarophile. Also for the first time, β-amino ketones (Mannich bases) were used as dipolarophile equivalents of unsaturated ketones. It was found that cycloaddition occurs diastereoselectively at the generated center. MDPI 2017-12-04 /pmc/articles/PMC6149807/ /pubmed/29207519 http://dx.doi.org/10.3390/molecules22122134 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
Anis’kov, Alexander
Klochkova, Irina
Tumskiy, Roman
Yegorova, Alevtina
A Diastereoselective Synthesis of Dispiro[oxindole-cyclohexanone]pyrrolidines by 1,3-Dipolar Cycloaddition
title A Diastereoselective Synthesis of Dispiro[oxindole-cyclohexanone]pyrrolidines by 1,3-Dipolar Cycloaddition
title_full A Diastereoselective Synthesis of Dispiro[oxindole-cyclohexanone]pyrrolidines by 1,3-Dipolar Cycloaddition
title_fullStr A Diastereoselective Synthesis of Dispiro[oxindole-cyclohexanone]pyrrolidines by 1,3-Dipolar Cycloaddition
title_full_unstemmed A Diastereoselective Synthesis of Dispiro[oxindole-cyclohexanone]pyrrolidines by 1,3-Dipolar Cycloaddition
title_short A Diastereoselective Synthesis of Dispiro[oxindole-cyclohexanone]pyrrolidines by 1,3-Dipolar Cycloaddition
title_sort diastereoselective synthesis of dispiro[oxindole-cyclohexanone]pyrrolidines by 1,3-dipolar cycloaddition
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6149807/
https://www.ncbi.nlm.nih.gov/pubmed/29207519
http://dx.doi.org/10.3390/molecules22122134
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