Please use this identifier to cite or link to this item:
https://hdl.handle.net/2440/18011
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Full metadata record
DC Field | Value | Language |
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dc.contributor.author | Greatrex, B. | - |
dc.contributor.author | Kimber, M. | - |
dc.contributor.author | Taylor, D. | - |
dc.contributor.author | Tiekink, E. | - |
dc.date.issued | 2003 | - |
dc.identifier.citation | Journal of Organic Chemistry, 2003; 68(11):4239-4246 | - |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.issn | 1520-6904 | - |
dc.identifier.uri | http://hdl.handle.net/2440/18011 | - |
dc.description | Copyright © 2003 American Chemical Society | - |
dc.description.abstract | An approach to highly functionalized tetrahydrofuran derivatives based upon a novel Oxa-Michael/ Michael dimerization of cis- γ-hydroxyenones is presented. The reaction begins with either 1,2- dioxines or trans- γ-hydroxyenones and proceeds by addition of one molecule of trans- γ-hydroxyenone to another molecule of cis- or trans- γ-hydroxyenone catalyzed by an alkoxide or hydroxide base. Subsequent intramolecular Michael addition of the keto-enolate gives the observed tetrahydrofurans. Substitution at both the 2- and 4-positions of the γ-hydroxyenone is tolerated; however, for 4-substituted γ-hydroxyenones, selectivity issues arise due to the possibility of heterochiral or homochiral dimerizations. The major products were those with all contiguous groups trans. | - |
dc.description.statementofresponsibility | Ben W. Greatrex, Marc C. Kimber, Dennis K. Taylor, and Edward R. T. Tiekink | - |
dc.language.iso | en | - |
dc.publisher | Amer Chemical Soc | - |
dc.source.uri | http://pubs.acs.org/cgi-bin/abstract.cgi/joceah/2003/68/i11/abs/jo020700h.html | - |
dc.title | A novel synthesis of functionalized tetrahydrofurans by an oxa-Michael/Michael cyclization of g-hydroxyenones | - |
dc.type | Journal article | - |
dc.identifier.doi | 10.1021/jo020700h | - |
pubs.publication-status | Published | - |
dc.identifier.orcid | Taylor, D. [0000-0002-3302-4610] [0000-0002-4274-3983] [0000-0003-0633-7424] | - |
Appears in Collections: | Aurora harvest 2 Chemistry publications |
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