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http://hdl.handle.net/2445/63194
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DC Field | Value | Language |
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dc.contributor.author | Petit, Elena | - |
dc.contributor.author | Bosch Hereu, Lluís | - |
dc.contributor.author | Font, Joan | - |
dc.contributor.author | Mola Solà, Laura | - |
dc.contributor.author | Costa i Arnau, Anna M. | - |
dc.contributor.author | Vilarrasa i Llorens, Jaume | - |
dc.date.accessioned | 2015-02-20T12:19:49Z | - |
dc.date.available | 2015-08-27T22:01:40Z | - |
dc.date.issued | 2014-08-27 | - |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.uri | http://hdl.handle.net/2445/63194 | - |
dc.description.abstract | The use of the 2-(4-methylphenylsulfonyl)ethenyl (tosvinyl, Tsv) group for the protection of the NH group of a series of imides, azinones (including AZT), inosines, and cyclic sulfonamides has been examined. The Tsv-protected derivatives are obtained in excellent yields by conjugate addition to tosylacetylene (ethynyl p-tolyl sulfone). The stereochemistry of the double bond can be controlled at will: with only 1 mol % of Et3N or with catalytic amounts of NaH, the Z stereoisomers are generated almost exclusively, while the E isomers are obtained using a stoichiometric amount of DMAP. Analogous phenylsulfonylvinyl-protected groups (with the besvinyl or Bsv group instead of Tsv) are obtained stereospecifically by reaction with (Z)- or (E)-bis(phenylsulfonyl)ethene. For lactams and oxazolidinones, this last method is much better. The Tsv and Bsv groups are stable in the presence of non-nucleophilic bases and to acids. They can be removed highly effectively via a conjugate addition-elimination mechanism using pyrrolidine or sodium dodecanethiolate as nucleophiles. | - |
dc.format.extent | 22 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/jo501647w | - |
dc.relation.ispartof | Journal of Organic Chemistry, 2014, vol. 79, num. 18, p. 8826-8834 | - |
dc.relation.uri | http://dx.doi.org/10.1021/jo501647w | - |
dc.rights | (c) American Chemical Society , 2014 | - |
dc.source | Articles publicats en revistes (Química Inorgànica i Orgànica) | - |
dc.subject.classification | Estereoquímica | - |
dc.subject.classification | Compostos heterocíclics | - |
dc.subject.classification | Catàlisi | - |
dc.subject.classification | Síntesi orgànica | - |
dc.subject.classification | Proves i reactius químics | - |
dc.subject.other | Stereochemistry | - |
dc.subject.other | Heterocyclic compounds | - |
dc.subject.other | Catalysis | - |
dc.subject.other | Organic synthesis | - |
dc.subject.other | Chemical tests and reagents | - |
dc.title | Tosvinyl and besvinyl as protecting groups of imides, azinones, nucleosides, sultams, and lactams. Catalytic conjugate additions to tosylacetylene. | - |
dc.type | info:eu-repo/semantics/article | - |
dc.type | info:eu-repo/semantics/acceptedVersion | - |
dc.identifier.idgrec | 646926 | - |
dc.date.updated | 2015-02-20T12:19:49Z | - |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | - |
Appears in Collections: | Articles publicats en revistes (Química Inorgànica i Orgànica) |
Files in This Item:
File | Description | Size | Format | |
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646926.pdf | 518.8 kB | Adobe PDF | View/Open |
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