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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...

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Autores principales: Griffiths, Oliver M., Ley, Steven V.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
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.
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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.
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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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