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https://hdl.handle.net/2440/61717
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dc.contributor.author | Zvarec, O. | - |
dc.contributor.author | Avery, T. | - |
dc.contributor.author | Taylor, D. | - |
dc.contributor.author | Tiekink, E. | - |
dc.date.issued | 2010 | - |
dc.identifier.citation | Tetrahedron: the international journal for the rapid publication of full original research papers and critical reviews in organic chemistr, 2010; 66(4):1007-1013 | - |
dc.identifier.issn | 0040-4020 | - |
dc.identifier.uri | http://hdl.handle.net/2440/61717 | - |
dc.description.abstract | Herein we outline cyclisations of tethered hydroxyl and carboxylic acid moieties onto the olefinic motif of 1,2-dioxines to generate tetrahydrofurans and dihydrofuran-2(3H)-ones, whilst maintaining the peroxide linkage intact. This work demonstrates the first examples of intramolecular cyclisation of tethered hydroxyl groupings onto 1,2-dioxines generating functionalised THFs in a highly stereoselective manner and includes improved methods for previously reported carboxylic acid tether cyclisations. Additionally, improved methods for the oxidation of 1,2-dioxines containing tethered alcohols to furnish tethered carboxylic acids are also detailed. Subsequent reduction of the peroxide linkage enables the generation of functionalised tetrahydrofurans and dihydrofuran-2(3H)-ones, which are useful building blocks for the construction of natural products. © 2009 Elsevier Ltd. All rights reserved. | - |
dc.description.statementofresponsibility | Ondrej Zvarec, Thomas D. Avery, Dennis K. Taylor and Edward R.T. Tiekink | - |
dc.language.iso | en | - |
dc.publisher | Pergamon-Elsevier Science Ltd | - |
dc.rights | (c) 2009 Elsevier Ltd. All rights reserved | - |
dc.source.uri | http://dx.doi.org/10.1016/j.tet.2009.11.068 | - |
dc.subject | 1,2-Dioxine | - |
dc.subject | Tetrahydrofurans | - |
dc.subject | Dihydrofuran-2(3H)-ones | - |
dc.subject | Cyclisation | - |
dc.title | Cyclisation of 1,2-dioxines containing tethered hydroxyl and carboxylic acid functionality: synthesis of tetrahydrofurans and dihydrofuran-2(3H)-ones | - |
dc.type | Journal article | - |
dc.identifier.doi | 10.1016/j.tet.2009.11.068 | - |
dc.relation.grant | ARC | - |
pubs.publication-status | Published | - |
dc.identifier.orcid | Avery, T. [0000-0001-6882-5461] | - |
dc.identifier.orcid | Taylor, D. [0000-0002-3302-4610] [0000-0002-4274-3983] [0000-0003-0633-7424] | - |
Appears in Collections: | Aurora harvest 5 Chemistry publications |
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