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dc.contributor.author
Illa, Ona
dc.contributor.author
Muray, Elena
dc.contributor.author
Amsallem, Déborah
dc.contributor.author
Moglioni, Albertina Gladys
dc.contributor.author
Gornitzka, Heinz
dc.contributor.author
Branchadell, Vicenç
dc.contributor.author
Baceiredo, Antoine
dc.contributor.author
Ortuño, Rosa M.
dc.date.available
2021-12-28T11:45:53Z
dc.date.issued
2002-11
dc.identifier.citation
Illa, Ona; Muray, Elena; Amsallem, Déborah; Moglioni, Albertina Gladys; Gornitzka, Heinz; et al.; A comparative study on the 1,3-dipolar cycloadditions of diazomethane and bis(diisopropylamino)phosphinodiazomethane to chiral electron-deficient olefins: Reactivity and diastereoselectivity; Pergamon-Elsevier Science Ltd; Tetrahedron: Asymmetry; 13; 23; 11-2002; 2593-2603
dc.identifier.issn
0957-4166
dc.identifier.uri
http://hdl.handle.net/11336/149308
dc.description.abstract
The 1,3-dipolar cycloadditions of bis(diisopropylamino)phosphinodiazomethane, 10, to chiral electron-deficient olefins have been investigated for the first time. The results have been compared with those corresponding to the reactions of diazomethane and the same or similar substrates. The experimental observations have been rationalized by DFT theoretical calculations. Diazomethane has been shown to be more reactive than 10 in all cases. The dipolarophiles include compounds synthesized from D-glyceraldehyde acetonide and (-)-verbenone. The latter compounds, bearing a gem-dimethylcyclobutane moiety, are less reactive than those derived from D-glyceraldehyde bearing a dioxolane ring. The influence of the Z/E geometry of the double bond on the reactivity and the π-facial diastereoselectivity has been investigated. Thus, in the reactions of diazomethane, the diastereoselectivity is not dependent on the Z/E stereochemistry but the reactivity is lower for (E)-cyclobutyl derivatives than for their Z isomers. In the reactions between 10 and the glyceraldehyde derivatives, the E isomers are less reactive than the Z ones and afford adducts with poor facial diastereoselectivity due to unfavorable interactions between the reactants in the corresponding transition states.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Pergamon-Elsevier Science Ltd
dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject.classification
Farmacología y Farmacia
dc.subject.classification
Medicina Básica
dc.subject.classification
CIENCIAS MÉDICAS Y DE LA SALUD
dc.title
A comparative study on the 1,3-dipolar cycloadditions of diazomethane and bis(diisopropylamino)phosphinodiazomethane to chiral electron-deficient olefins: Reactivity and diastereoselectivity
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2021-12-03T20:50:50Z
dc.journal.volume
13
dc.journal.number
23
dc.journal.pagination
2593-2603
dc.journal.pais
Estados Unidos
dc.description.fil
Fil: Illa, Ona. Universitat Autònoma de Barcelona; España
dc.description.fil
Fil: Muray, Elena. Universitat Autònoma de Barcelona; España
dc.description.fil
Fil: Amsallem, Déborah. Université Paul Sabatier; Francia
dc.description.fil
Fil: Moglioni, Albertina Gladys. Universitat Autònoma de Barcelona; España. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
dc.description.fil
Fil: Gornitzka, Heinz. Université Paul Sabatier; Francia
dc.description.fil
Fil: Branchadell, Vicenç. Universitat Autònoma de Barcelona; España
dc.description.fil
Fil: Baceiredo, Antoine. Université Paul Sabatier; Francia
dc.description.fil
Fil: Ortuño, Rosa M.. Universitat Autònoma de Barcelona; España
dc.journal.title
Tetrahedron: Asymmetry
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0957416602007140
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1016/S0957-4166(02)00714-0
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