Asymmetric construction of substituted pyrrolidines via 1,3-dipolar cycloaddition of azomethine ylides and chiral acrylates derived from biomass |
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| Authors: | David F. Llompart,Ariel M. Sarotti,Valeria Corne,Alejandra G. Suá rez,Rolando A. Spanevello,Gustavo A. Echeverrí a,Oscar E. Piro,Eduardo E. Castellano |
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| Affiliation: | 1. Instituto de Química Rosario (IQUIR), Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario–CONICET, Suipacha 531, S2002LRK Rosario, Argentina;2. Instituto de Física de La Plata (CONICET, CCT-La Plata) and Departamento de Física, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, C.C. 67, 1900 La Plata, Argentina;3. Instituto de Física de São Carlos, Universidade de São Paulo, C.P. 369, 13560 São Carlos (SP), Brazil |
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| Abstract: | 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. |
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| Keywords: | Levoglucosenone Chiral auxiliaries 1,3-Dipolar cycloaddition Azomethine ylides GIAO NMR calculations |
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