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

✍ Scribed by Bor-Cherng Hong; Kwan-Liang Liu; Chih-Wei Tsai; Ju-Hsiou Liao

Book ID: 104095608
Publisher: Elsevier Science
Year: 2008
Tongue: French
Weight: 224 KB
Volume: 49
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2008.07.039

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✦ Synopsis

1,3-Dipolar cycloaddition reaction of cinnamaldehyde with azomethine ylides generated through decarboxylation 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.

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