Mostrar el registro sencillo del ítem
dc.contributor.author
Cankarova, Nadezda
dc.contributor.author
la Venia, Agustina
dc.contributor.author
Krajcovicova, Sona
dc.contributor.author
Krchnak, Viktor
dc.date.available
2019-10-23T20:46:39Z
dc.date.issued
2019-01
dc.identifier.citation
Cankarova, Nadezda; la Venia, Agustina; Krajcovicova, Sona; Krchnak, Viktor; Configuration-Dependent Medium-Sized Ring Formation: Chiral Molecular Framework with Three-Dimensional Architecture; American Chemical Society; Journal of Organic Chemistry; 84; 2; 1-2019; 636-644
dc.identifier.issn
0022-3263
dc.identifier.uri
http://hdl.handle.net/11336/87173
dc.description.abstract
This report describes a configuration-dependent [6 + 8 + 5] fused ring formation via a tandem cyclic N-acyliminium nucleophilic addition reaction. Cyclization of the acyclic precursor prepared on a solid phase using l-Ser and a racemic mixture of Fmoc-trans-2-aminocyclohexanecarboxylic acid predominantly yielded the cyclic diastereomer with the (1R,2R)-2-aminocyclohexane moiety rather than the tricyclic diastereomer from the (1S,2S)-enantiomer. In contrast, the model compound prepared with d-Ser predominantly cyclized with the (1S,2S)-2-aminocyclohexanecarboxylic acid substrate. The outcome of the cyclization was not influenced by the type of resin, the spacer, or the N-substituent. The analogous synthesis of the [6 + 7 + 5] fused ring system yielded inseparable diastereomers in a 1:0.6 ratio.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
American Chemical Society
dc.rights
info:eu-repo/semantics/embargoedAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
3D ARCHITECTURE
dc.subject
ABSOLUTE CONFIGURATION
dc.subject
HETEROCYCLES
dc.subject
MEDIUM-SIZED RINGS
dc.subject
MOLECULAR SCAFFOLD
dc.subject
SOLID-PHASE SYNTHESIS
dc.subject.classification
Química Orgánica
dc.subject.classification
Ciencias Químicas
dc.subject.classification
CIENCIAS NATURALES Y EXACTAS
dc.title
Configuration-Dependent Medium-Sized Ring Formation: Chiral Molecular Framework with Three-Dimensional Architecture
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2019-10-16T19:29:48Z
dc.journal.volume
84
dc.journal.number
2
dc.journal.pagination
636-644
dc.journal.pais
Estados Unidos
dc.description.fil
Fil: Cankarova, Nadezda. Palacky University; República Checa
dc.description.fil
Fil: la Venia, Agustina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
dc.description.fil
Fil: Krajcovicova, Sona. Palacky University; República Checa
dc.description.fil
Fil: Krchnak, Viktor. Palacky University; República Checa
dc.journal.title
Journal of Organic Chemistry
dc.rights.embargoDate
2020-01-01
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1021/acs.joc.8b02465
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/acs.joc.8b02465
Archivos asociados