Mostrar el registro sencillo del ítem
dc.contributor.author
Gerbino, Darío César
dc.contributor.author
Koll, Liliana Cristina
dc.contributor.author
Mandolesi, Sandra Delia
dc.contributor.author
Podestá, Julio Cesar
dc.date.available
2018-12-05T18:33:37Z
dc.date.issued
2008-02
dc.identifier.citation
Gerbino, Darío César; Koll, Liliana Cristina; Mandolesi, Sandra Delia; Podestá, Julio Cesar; Stereoselective radical tandem cyclohydrostannation of optically active di-unsaturated esters of TADDOL; American Chemical Society; Organometallics; 27; 4; 2-2008; 660-665
dc.identifier.issn
0276-7333
dc.identifier.uri
http://hdl.handle.net/11336/65893
dc.description.abstract
This paper reports the results obtained in a study on the radical addition of triorganotin hydrides, R3SnH (R = Me, n-Bu, Ph; Neophyl), to four TADDOL unsaturated diesters. It was found that diese reactions lead in high yields to products of cyclohydrostannation. It was also found that whereas the addition of these hydrides to TADDOL diacrylate and TADDOL dimethacrylate leads to the expected mixtures of two and four cycloundecane diastereoisomers, respectively, the addition of triphenyltin hydride to TADDOL disubstituted acrylates yields only four out of the 16 possible stereoisomers. The observed high stereoselectivity is consistent with the radical tandem cyclohydrostannation mechanism proposed. Only in the case of the hydrostannation of TADDOL diacrylate with trimethyl- and triphenyltin hydrides could the diastereoisomers obtained in higher proportion (5a and 8a) be isolated in pure form. The subsequent reduction (lithium aluminum hydride) of macrolides 5a and 8a afforded the corresponding optically active diols 26 and 27 in high yield. Full 1H, 13C, and 119Sn NMR data are given. © 2008 American Chemical Society.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
American Chemical Society
dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
Hydrostannation
dc.subject
Taddol
dc.subject
Enantioselective Reaction
dc.subject.classification
Otras Ciencias Químicas
dc.subject.classification
Ciencias Químicas
dc.subject.classification
CIENCIAS NATURALES Y EXACTAS
dc.title
Stereoselective radical tandem cyclohydrostannation of optically active di-unsaturated esters of TADDOL
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2018-11-22T14:28:44Z
dc.journal.volume
27
dc.journal.number
4
dc.journal.pagination
660-665
dc.journal.pais
Estados Unidos
dc.journal.ciudad
Columbus
dc.description.fil
Fil: Gerbino, Darío César. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
dc.description.fil
Fil: Koll, Liliana Cristina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
dc.description.fil
Fil: Mandolesi, Sandra Delia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
dc.description.fil
Fil: Podestá, Julio Cesar. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
dc.journal.title
Organometallics
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/https://dx.doi.org/10.1021/om700693p
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/full/10.1021/om700693p
Archivos asociados