## Abstract Azomethine ylides generated from 5β(alkoxycarbonylmethyl)phenanthridinium cations were studied in 1,3βdipolar cycloadditions with dimethyl maleate and dimethyl fumarate as dipolarophiles. The cycloadducts with the pyrrolidino[1,2βf]phenanthridine skeleton easily underwent dehydrogenatio
1,3 Dipolar cycloadditions of azomethine ylides with aromatic aldehydes. syntheses of 1-oxapyrrolizidines and 1,3-oxazolidines.
β Scribed by F. Orsini; F. Pelizzoni; M. Forte; R. Destro; P. Gariboldi
- Publisher
- Elsevier Science
- Year
- 1988
- Tongue
- French
- Weight
- 965 KB
- Volume
- 44
- Category
- Article
- ISSN
- 0040-4020
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β¦ Synopsis
Substituted 1-oxapyrrolizidines have been synthetized by cycloaddition of azomethi?e ylides, generated by aldehydes induced decarboxylation of proline, with dipolarophylei.' The carbonyl stbreochernistry of the cycloadducts indicate that they arise from the stereospecific formation of one is6mer of the azomethine ylide.
π SIMILAR VOLUMES
Methods are described of synthesizing various 3-carboxy-4-vinyl pyrrolidines, versatile building blocks for our drug discovery efforts. The 1,3-dipolar cycloaddition between activated olefins and nonstabilized azomethine ylide is a known method for synthesizing pyrrolidines in a stereospecific manne