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Multicomponent Direct Assembly of N-Heterospirocycles Facilitated by Visible-Light-Driven Photocatalysis
[Image: see text] N-heterospirocycles are interesting structural units found in both natural products and medicinal compounds but have relatively few reliable methods for their synthesis. Here, we enlist the photocatalytic generation of N-centered radicals to construct β-spirocyclic pyrrolidines fro...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2022
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9552240/ https://www.ncbi.nlm.nih.gov/pubmed/36103403 http://dx.doi.org/10.1021/acs.joc.2c01684 |
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author | Griffiths, Oliver M. Ley, Steven V. |
author_facet | Griffiths, Oliver M. Ley, Steven V. |
author_sort | Griffiths, Oliver M. |
collection | PubMed |
description | [Image: see text] N-heterospirocycles are interesting structural units found in both natural products and medicinal compounds but have relatively few reliable methods for their synthesis. Here, we enlist the photocatalytic generation of N-centered radicals to construct β-spirocyclic pyrrolidines from N-allylsulfonamides and alkenes. A variety of β-spirocyclic pyrrolidines have been constructed, including drug derivatives, in moderate to very good yields. Further derivatization of the products has also been demonstrated as has a viable scale-up procedure, making use of flow chemistry techniques. |
format | Online Article Text |
id | pubmed-9552240 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-95522402022-10-12 Multicomponent Direct Assembly of N-Heterospirocycles Facilitated by Visible-Light-Driven Photocatalysis Griffiths, Oliver M. Ley, Steven V. J Org Chem [Image: see text] N-heterospirocycles are interesting structural units found in both natural products and medicinal compounds but have relatively few reliable methods for their synthesis. Here, we enlist the photocatalytic generation of N-centered radicals to construct β-spirocyclic pyrrolidines from N-allylsulfonamides and alkenes. A variety of β-spirocyclic pyrrolidines have been constructed, including drug derivatives, in moderate to very good yields. Further derivatization of the products has also been demonstrated as has a viable scale-up procedure, making use of flow chemistry techniques. American Chemical Society 2022-09-14 2022-10-07 /pmc/articles/PMC9552240/ /pubmed/36103403 http://dx.doi.org/10.1021/acs.joc.2c01684 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Griffiths, Oliver M. Ley, Steven V. Multicomponent Direct Assembly of N-Heterospirocycles Facilitated by Visible-Light-Driven Photocatalysis |
title | Multicomponent Direct
Assembly of N-Heterospirocycles Facilitated
by Visible-Light-Driven Photocatalysis |
title_full | Multicomponent Direct
Assembly of N-Heterospirocycles Facilitated
by Visible-Light-Driven Photocatalysis |
title_fullStr | Multicomponent Direct
Assembly of N-Heterospirocycles Facilitated
by Visible-Light-Driven Photocatalysis |
title_full_unstemmed | Multicomponent Direct
Assembly of N-Heterospirocycles Facilitated
by Visible-Light-Driven Photocatalysis |
title_short | Multicomponent Direct
Assembly of N-Heterospirocycles Facilitated
by Visible-Light-Driven Photocatalysis |
title_sort | multicomponent direct
assembly of n-heterospirocycles facilitated
by visible-light-driven photocatalysis |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9552240/ https://www.ncbi.nlm.nih.gov/pubmed/36103403 http://dx.doi.org/10.1021/acs.joc.2c01684 |
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