Proline-mediated dimerization of cinnamaldehydes via 1,3-dipolar cycloaddition reaction with azomethine ylides.: A rapid access to highly functionalized hexahydro-1H-pyrrolizine

1,3-Dipolar cycloaddition reaction of cinnamaldehyde with azomethine ylides generated through decaboxylation of iminium or oxazolidinone intermediate formed by the reaction Of L-proline with cinnamaldehydes is reported. The stereoselective reaction provides an efficient access to the highly functionalized hexahydro-1H-pyrrolizine. (C) 2008 Elsevier Ltd. All rights reserved.