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2013-05-28

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Si us plau utilitzeu sempre aquest identificador per citar o enllaçar aquest document: https://hdl.handle.net/2445/53365

Nucleophile-Catalyzed Additions to Activated Triple Bonds. Protection of Lactams, Imides, and Nucleosides with MocVinyl and Related Groups

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http://dx.doi.org/10.1021/jo4006409

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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.

Matèries

Síntesi orgànica, Amines, Catalitzadors, Lactames, Nucleòsids, Proves i reactius químics

Matèries (anglès)

Organic synthesis, Amines, Catalysts, Lactams, Nucleosides, Chemical tests and reagents

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Articles publicats en revistes (Química Inorgànica i Orgànica)

Citació

MOLA SOLÀ, Laura, FONT, Joan, BOSCH HEREU, Lluís, CANER, Joaquim, COSTA I ARNAU, Anna m., ETXEBARRÍA-JARDÍ, Gorka, PINEDA, Oriol, VICENTE, David d., VILARRASA I LLORENS, Jaume. Nucleophile-Catalyzed Additions to Activated Triple Bonds. Protection of Lactams, Imides, and Nucleosides with MocVinyl and Related Groups. _Journal of Organic Chemistry_. 2013. Vol. 78, núm. 12, pàgs. 5832-5842. [consulta: 15 de febrer de 2026]. ISSN: 0022-3263. [Disponible a: https://hdl.handle.net/2445/53365]

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