Effect of tether length on endo/exo stereoselectivity in alkene–arene meta‐photocycloaddition reactions towards the Aphidocolin/Stemodin scaffolds

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Alshammari, A. A. A., Boyd, J. W., Greaves, N., Kettle, J. G., McKendrick, J. E. ORCID: https://orcid.org/0000-0003-2275-0569, Parker, L. G., Russell, A. T., Sani, A. and Smith, C. D. ORCID: https://orcid.org/0000-0002-5911-5836 (2024) Effect of tether length on endo/exo stereoselectivity in alkene–arene meta‐photocycloaddition reactions towards the Aphidocolin/Stemodin scaffolds. European Journal of Organic Chemistry. ISSN 1099-0690 (In Press)

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To link to this item DOI: 10.1002/ejoc.202400463

Abstract/Summary

Intramolecular alkene-arene meta-photocycloadditions are powerful transformations that use the enhanced reactivity of photoexcited benzene rings to facilitate addition of an alkene 1,3 across donor groups and form complex three-dimensional fused-ring systemsfrom readily accessible starting materials. Intramolecular examples havetraditionallybeen restricted to 3-memberedtethers, with cycloaddition resulting from exo-conformation. However, by judicious tether design we have demonstratedthat a 4-membered tether can also proceed in good yield; interestingly,viaan endo-exciplex(1.2:1) enabling access to both natural product skeletons and interesting scaffolds for medicinal chemistry research.

Item Type:	Article
Refereed:	Yes
Divisions:	Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry Interdisciplinary centres and themes > Chemical Analysis Facility (CAF) > Mass Spectrometry (CAF) Interdisciplinary centres and themes > Chemical Analysis Facility (CAF) > NMR (CAF) Interdisciplinary centres and themes > Chemical Analysis Facility (CAF) > Optical Spectroscopy (CAF) Interdisciplinary centres and themes > Chemical Analysis Facility (CAF) > Xray (CAF)
ID Code:	116221
Uncontrolled Keywords:	meta-Photocycloaddition; Photochemistry; Aphidicolin; Stemodin; Flow
Publisher:	European Chemical Societies Publishing

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Effect of tether length on endo/exo stereoselectivity in alkene–arene meta‐photocycloaddition reactions towards the Aphidocolin/Stemodin scaffolds

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