XY–ZH systems as potential 1,3-dipoles. Part 11. Stereochemistry of 1,3-dipoles generated by the decarboxylative route to azomethine ylides
| Autor: | S. Thianpatanagul, D. Vipond, Sivagnanasundram Surendrakumar, Ronald Grigg |
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| Rok vydání: | 1988 |
| Předmět: | |
| Zdroj: | J. Chem. Soc., Perkin Trans. 1. :2693-2701 |
| ISSN: | 1364-5463 0300-922X |
| DOI: | 10.1039/p19880002693 |
| Popis: | The decarboxylative reaction of aryl aldehydes with cyclic secondary α-amino acids or primary α-amino acids in the presence of N-methyl- or N-phenyl-maleimide leads, via an intermediate azomethine ylide, to mixtures of bicyclic pyrrolidine cycloadducts in good yield. Cyclic secondary α-amino acids, where the carboxylic group is non-benzylic, give cycloadducts arising from a stereospecifically generated anti-dipole. Acyclic α-amino acids, and cyclic secondary α-amino acids with the carboxylic group located at a benzylic site, give rise to cycloadducts derived from both anti- and syn-configurations of the intermediate azomethine glides. The reactions show little discrimination between endo- and exo-transition states for the cycloadditions. |
| Databáze: | OpenAIRE |
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