Asymmetric construction of substituted pyrrolidines via 1,3-dipolar cycloaddition of azomethine ylides and chiral acrylates derived from biomass

dc.creatorLlompart, David Fernando
dc.creatorSarotti, Ariel Marcelo
dc.creatorCorne, Valeria
dc.creatorSuarez, Alejandra Graciela
dc.creatorSpanevello, Rolando Angel
dc.creatorEcheverría, Gustavo Alberto
dc.creatorPiro, Oscar Enrique
dc.creatorCastellano, Eduardo E.
dc.date.accessioned2017-10-09T21:07:22Z
dc.date.accessioned2018-11-06T11:29:40Z
dc.date.available2017-10-09T21:07:22Z
dc.date.available2018-11-06T11:29:40Z
dc.date.created2017-10-09T21:07:22Z
dc.date.issued2014-03
dc.identifierLlompart, David Fernando; Sarotti, Ariel Marcelo; Corne, Valeria; Suarez, Alejandra Graciela; Spanevello, Rolando Angel; et al.; Asymmetric construction of substituted pyrrolidines via 1,3-dipolar cycloaddition of azomethine ylides and chiral acrylates derived from biomass; Elsevier; Tetrahedron Letters; 55; 15; 3-2014; 2394-2397
dc.identifier0040-4039
dc.identifierhttp://hdl.handle.net/11336/26299
dc.identifierCONICET Digital
dc.identifierCONICET
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1853369
dc.description.abstractThe first application of chiral auxiliaries synthesized from levoglucosenone (a biomass-derived anhydrosugar) in asymmetric 1,3-dipolar cycloaddition reactions of azomethine ylides is herein reported. The corresponding pyrrolidinic cores were obtained in excellent levels of regio and stereocontrol, good to excellent π-facial selectivities, and could be isolated enantiomerically pure by column chromatography. Unexpected NMR observations coupled with DFT calculations allowed the stereochemical assignment of the synthesized adducts. The stereochemical assignment performed in silico was further unambiguously validated by structural X-ray diffraction analysis.
dc.languageeng
dc.publisherElsevier
dc.relationinfo:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1016/j.tetlet.2014.02.113
dc.relationinfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0040403914003657
dc.rightshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.rightsinfo:eu-repo/semantics/restrictedAccess
dc.subjectAZOMETHINE YLIDES
dc.subject1,3-DIPOLAR CYCLOADDITION
dc.subjectLEVOGLUCOSENONE
dc.subjectCHIRAL AUXILIARIES
dc.titleAsymmetric construction of substituted pyrrolidines via 1,3-dipolar cycloaddition of azomethine ylides and chiral acrylates derived from biomass
dc.typeArtículos de revistas
dc.typeArtículos de revistas
dc.typeArtículos de revistas


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