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http://hdl.handle.net/2445/53365
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DC Field | Value | Language |
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dc.contributor.author | Mola Solà, Laura | - |
dc.contributor.author | Font, Joan | - |
dc.contributor.author | Bosch Hereu, Lluís | - |
dc.contributor.author | Caner, Joaquim | - |
dc.contributor.author | Costa i Arnau, Anna M. | - |
dc.contributor.author | Etxebarría-Jardí, Gorka | - |
dc.contributor.author | Pineda, Oriol | - |
dc.contributor.author | Vicente, David D. | - |
dc.contributor.author | Vilarrasa i Llorens, Jaume | - |
dc.date.accessioned | 2014-04-08T13:29:49Z | - |
dc.date.available | 2014-05-28T22:02:24Z | - |
dc.date.issued | 2013-05-28 | - |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.uri | http://hdl.handle.net/2445/53365 | - |
dc.description.abstract | Additions of lactams, imides, (S)-4-benzyl-1,3-oxazolidin-2-one, 2-pyridone, pyrimidine-2,4-diones (AZT derivatives), or inosines to the electron-deficient triple bonds of methyl propynoate, tert-butyl propynoate, 3-butyn-2-one, N-propynoylmorpholine, or N-methoxy-N-methylpropynamide in the presence of many potential catalysts were examined. DABCO and, second, DMAP appeared to be the best (highest reaction rates and E/Z ratios), while RuCl3, RuClCp*(PPh3)2, AuCl, AuCl(PPh3), CuI, and Cu2(OTf)2 were incapable of catalyzing such additions. The groups incorporated (for example, the 2-(methoxycarbonyl)ethenyl group that we name MocVinyl) serve as protecting groups for the above-mentioned heterocyclic CONH or CONHCO moieties. Deprotections were accomplished via exchange with good nucleophiles: the 1-dodecanethiolate anion turned out to be the most general and efficient reagent, but in some particular cases other nucleophiles also worked (e.g., MocVinyl-inosines can be cleaved with succinimide anion). Some structural and mechanistic details have been accounted for with the help of DFT and MP2 calculations. | - |
dc.format.extent | 25 p. | - |
dc.format.mimetype | application/pdf | - |
dc.language.iso | eng | - |
dc.publisher | American Chemical Society | - |
dc.relation.isformatof | Versió postprint del document publicat a: http://dx.doi.org/10.1021/jo4006409 | - |
dc.relation.ispartof | Journal of Organic Chemistry, 2013, vol. 78, num. 12, p. 5832-5842 | - |
dc.relation.uri | http://dx.doi.org/10.1021/jo4006409 | - |
dc.rights | (c) American Chemical Society , 2013 | - |
dc.source | Articles publicats en revistes (Química Inorgànica i Orgànica) | - |
dc.subject.classification | Síntesi orgànica | - |
dc.subject.classification | Amines | - |
dc.subject.classification | Catalitzadors | - |
dc.subject.classification | Lactames | - |
dc.subject.classification | Nucleòsids | - |
dc.subject.classification | Proves i reactius químics | - |
dc.subject.other | Organic synthesis | - |
dc.subject.other | Amines | - |
dc.subject.other | Catalysts | - |
dc.subject.other | Lactams | - |
dc.subject.other | Nucleosides | - |
dc.subject.other | Chemical tests and reagents | - |
dc.title | Nucleophile-Catalyzed Additions to Activated Triple Bonds. Protection of Lactams, Imides, and Nucleosides with MocVinyl and Related Groups | eng |
dc.type | info:eu-repo/semantics/article | - |
dc.type | info:eu-repo/semantics/acceptedVersion | - |
dc.identifier.idgrec | 637401 | - |
dc.date.updated | 2014-04-03T07:13:07Z | - |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | - |
dc.identifier.pmid | 23713491 | - |
Appears in Collections: | Articles publicats en revistes (Química Inorgànica i Orgànica) |
Files in This Item:
File | Description | Size | Format | |
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637401.pdf | 567.61 kB | Adobe PDF | View/Open |
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