Artículos de revistas
Asymmetric construction of substituted pyrrolidines via 1,3-dipolar cycloaddition of azomethine ylides and chiral acrylates derived from biomass
Fecha
2014-03Registro en:
Llompart, 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
0040-4039
CONICET Digital
CONICET
Autor
Llompart, David Fernando
Sarotti, Ariel Marcelo
Corne, Valeria
Suarez, Alejandra Graciela
Spanevello, Rolando Angel
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Castellano, Eduardo E.
Resumen
The 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.