Synthesis of polycyclic lactams via intramolecular dipolar cycloadditions of stabilized azomethine ylides
โ Scribed by Stephen F. Martin; Tom H. Cheavens
- Publisher
- Elsevier Science
- Year
- 1989
- Tongue
- French
- Weight
- 238 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
A stereoselective two step sequence for the construction of fused pyrrolidone ring systems has been developed which features the intramolecular [3+2] dipolar cycloaddition of unsaturated azomethine ylides. The ylides are produced upon reaction of aminomethylphosphonates with so-olefimic aldehydes, followed by oxidative removal of the phosphonate ester group using a newly developed method.
๐ SIMILAR VOLUMES
On thermal treatment of the aziridines Sa-f intramolecular cycloaddition reactions of the intermedsteazomethine ylides 6 result in the formation of the metacyclophanes L-9. FoF 7a and 7b the conformational barriers are estimated to-be app';;;ximatzy 20 and 12 kcal/mol, respectively.
1,3-Dipolar cycloaddition of D-glucose-derived azomethine ylides for the synthesis of chiral pyrrolidines accompanied an unexpected 1,2-elimination in the furanose moiety of the products. The C3 0 alkoxy/ hydroxy group of the furanose moiety was invariably eliminated under the reaction conditions. A