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

作者：Llompart David F; Sarotti Ariel M^*; Corne Valeria; Suarez Alejandra G; Spanevello Rolando A; Echeverria Gustavo A; Piro Oscar E; Castellano Eduardo E

来源：Tetrahedron Letters, 2014, 55(15): 2394-2397.

DOI：10.1016/j.tetlet.2014.02.113

• Levoglucosenone
• Chiral auxiliaries
• 1,3-Dipolar cycloaddition
• Azomethine ylides
• GIAO NMR calculations

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 pi-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.

• 出版日期2014-4-9