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dc.contributor.author
Moglioni, Albertina Gladys
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dc.contributor.author
Muray, Elena
dc.contributor.author
Castillo, José A.
dc.contributor.author
Álvarez Larena, Ángel
dc.contributor.author
Moltrasio, Graciela Y.
dc.contributor.author
Branchadell, Vicenç
dc.contributor.author
Ortuño, Rosa M.
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dc.date.available
2021-08-13T14:34:40Z
dc.date.issued
2002-12
dc.identifier.citation
Moglioni, Albertina Gladys; Muray, Elena; Castillo, José A.; Álvarez Larena, Ángel; Moltrasio, Graciela Y.; et al.; Reaction between N-alkylhydroxylamines and chiral enoate esters: More experimental evidence for a cycloaddition-like process, a rationale based on DFT theoretical calculations, and stereoselective synthesis of new enantiopure β-amino acids; American Chemical Society; Journal of Organic Chemistry; 67; 8; 12-2002; 2402-2410
dc.identifier.issn
0022-3263
dc.identifier.uri
http://hdl.handle.net/11336/138276
dc.description.abstract
The reactions between N-benzyl- and N-methylhydroxylamine and chiral enoate esters, derived from D-glyceraldehyde and (-)-verbenone, respectively, have been investigated. Theoretical calculations show that the most favorable mechanism involves the concerted cycloaddition of the hydroxylamine to the substrate. This result is in good agreement with the stereospecificity observed when the trisubstituted olefins are used. The open-chain adducts have been isolated when the processes are carried out at low temperatures and for short reaction times. These compounds evolve to the corresponding isoxazolidinones on standing at room temperature or under acid catalysis. The high π-facial diastereoselection has been rationalized on the basis of steric effects induced by the dioxolane ring for D-glyceraldehyde derivatives or by the cyclobutane gem-dimethyl substitution for esters prepared from (-)-verbenone. As an application of these reactions, new β-amino acids have been synthesized in a highly efficient and stereocontrolled manner.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
American Chemical Society
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dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
(-)-verbenone
dc.subject
chiral enoate esters
dc.subject.classification
Farmacología y Farmacia
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dc.subject.classification
Medicina Básica
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dc.subject.classification
CIENCIAS MÉDICAS Y DE LA SALUD
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dc.title
Reaction between N-alkylhydroxylamines and chiral enoate esters: More experimental evidence for a cycloaddition-like process, a rationale based on DFT theoretical calculations, and stereoselective synthesis of new enantiopure β-amino acids
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2021-07-26T17:15:48Z
dc.journal.volume
67
dc.journal.number
8
dc.journal.pagination
2402-2410
dc.journal.pais
Estados Unidos
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dc.description.fil
Fil: Moglioni, Albertina Gladys. Universitat Autònoma de Barcelona; España. Universidad de Buenos Aires; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
dc.description.fil
Fil: Muray, Elena. Universitat Autònoma de Barcelona; España
dc.description.fil
Fil: Castillo, José A.. Universitat Autònoma de Barcelona; España
dc.description.fil
Fil: Álvarez Larena, Ángel. Universitat Autònoma de Barcelona; España
dc.description.fil
Fil: Moltrasio, Graciela Y.. Universidad de Buenos Aires; Argentina
dc.description.fil
Fil: Branchadell, Vicenç. Universitat Autònoma de Barcelona; España
dc.description.fil
Fil: Ortuño, Rosa M.. Universitat Autònoma de Barcelona; España
dc.journal.title
Journal of Organic Chemistry
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dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/jo0159082
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1021/jo0159082
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