Diastereoselective Synthesis of Highly Functionalized Proline Derivatives

An efficient way to access highly functionalized proline derivatives was developed based on a Cu(I)-catalyzed reaction between CF(3)-substituted allenynes and tosylazide, which involved a cascade of [3 + 2]-cycloaddition/ketenimine and a rearrangement/Alder-ene cyclization to afford the new proline...

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Autores principales: Philippova, Anna N., Vorobyeva, Daria V., Gribanov, Pavel S., Dolgushin, Fedor M., Osipov, Sergey N.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9609175/
https://www.ncbi.nlm.nih.gov/pubmed/36296490
http://dx.doi.org/10.3390/molecules27206898
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author Philippova, Anna N.
Vorobyeva, Daria V.
Gribanov, Pavel S.
Dolgushin, Fedor M.
Osipov, Sergey N.
author_facet Philippova, Anna N.
Vorobyeva, Daria V.
Gribanov, Pavel S.
Dolgushin, Fedor M.
Osipov, Sergey N.
author_sort Philippova, Anna N.
collection PubMed
description An efficient way to access highly functionalized proline derivatives was developed based on a Cu(I)-catalyzed reaction between CF(3)-substituted allenynes and tosylazide, which involved a cascade of [3 + 2]-cycloaddition/ketenimine and a rearrangement/Alder-ene cyclization to afford the new proline framework with a high diastereoselectivity.
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spelling pubmed-96091752022-10-28 Diastereoselective Synthesis of Highly Functionalized Proline Derivatives Philippova, Anna N. Vorobyeva, Daria V. Gribanov, Pavel S. Dolgushin, Fedor M. Osipov, Sergey N. Molecules Article An efficient way to access highly functionalized proline derivatives was developed based on a Cu(I)-catalyzed reaction between CF(3)-substituted allenynes and tosylazide, which involved a cascade of [3 + 2]-cycloaddition/ketenimine and a rearrangement/Alder-ene cyclization to afford the new proline framework with a high diastereoselectivity. MDPI 2022-10-14 /pmc/articles/PMC9609175/ /pubmed/36296490 http://dx.doi.org/10.3390/molecules27206898 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/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 (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Philippova, Anna N.
Vorobyeva, Daria V.
Gribanov, Pavel S.
Dolgushin, Fedor M.
Osipov, Sergey N.
Diastereoselective Synthesis of Highly Functionalized Proline Derivatives
title Diastereoselective Synthesis of Highly Functionalized Proline Derivatives
title_full Diastereoselective Synthesis of Highly Functionalized Proline Derivatives
title_fullStr Diastereoselective Synthesis of Highly Functionalized Proline Derivatives
title_full_unstemmed Diastereoselective Synthesis of Highly Functionalized Proline Derivatives
title_short Diastereoselective Synthesis of Highly Functionalized Proline Derivatives
title_sort diastereoselective synthesis of highly functionalized proline derivatives
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9609175/
https://www.ncbi.nlm.nih.gov/pubmed/36296490
http://dx.doi.org/10.3390/molecules27206898
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