Use of temporary tethers in the intramolecular [2+2] photocycloaddition reactions of tetrahydrophthalimide derivatives

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dc.authoridBaker, James/0000-0002-7223-2279
dc.contributor.authorGulten, Sirin
dc.contributor.authorSharpe, Andrew
dc.contributor.authorBaker, James R.
dc.contributor.authorBooker-Milburn, Kevin I.
dc.date.accessioned2025-01-27T20:11:42Z
dc.date.available2025-01-27T20:11:42Z
dc.date.issued2007
dc.departmentÇanakkale Onsekiz Mart Üniversitesi
dc.description.abstractThe intramolecular [2+2] photocycloaddition reactions of a series of alkenols tethered to ethanolamine, L-(+)-valinol and R-(-)-2-phenylglycinol derived 3,4,5,6-tetrahydrophthalimides via a carbonate or silicon linkage have been examined. These [2+2] photocycloadditions gave the corresponding cyclobutanes in high yield with complete endo control in all cases and with diastereoselectivities as high as 8:1 with the chiral tethers. The cleavage of the temporary tethers by either desilylation or hydrolysis provided the endo diols. Cleavage of the ethanolamine linkage by reduction/hydrolysis precipitated an acid-catalysed fragmentation/ring expansion sequence to generate complex tricyclic lactones. (C) 2007 Elsevier Ltd. All rights reserved.
dc.identifier.doi10.1016/j.tet.2007.02.064
dc.identifier.endpage3671
dc.identifier.issn0040-4020
dc.identifier.issue18
dc.identifier.scopus2-s2.0-33947656529
dc.identifier.scopusqualityQ3
dc.identifier.startpage3659
dc.identifier.urihttps://doi.org/10.1016/j.tet.2007.02.064
dc.identifier.urihttps://hdl.handle.net/20.500.12428/20684
dc.identifier.volume63
dc.identifier.wosWOS:000248202800002
dc.identifier.wosqualityQ1
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherPergamon-Elsevier Science Ltd
dc.relation.ispartofTetrahedron
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WoS_20250125
dc.subjectphotochemistry
dc.subjectcycloadditions
dc.subjecttemporary tethers
dc.subjectacidcatalysed rearrangements
dc.titleUse of temporary tethers in the intramolecular [2+2] photocycloaddition reactions of tetrahydrophthalimide derivatives
dc.typeArticle

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