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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