The indole-diketopiperazine bridge is an important structural feature of many bispyrrolidinoindoline and epipolythiodiketopiperazine fungal metabolites. Organocatalytic conjugate addition of diketopiperazines to indoles was achieved in good to excellent yields through electrophilic indolenine interm
Radical additions of simple piperazine-25-diones
✍ Scribed by Christina L.L. Chai; Dennis M. Page
- Publisher
- Elsevier Science
- Year
- 1993
- Tongue
- French
- Weight
- 245 KB
- Volume
- 34
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The polar character of a simple piperazine-2,S-dione was investigated under intermolecular radical addition conditions. 'Ihe results indicate that captodative radical of this kind neither show extreme nucleophilic nor electrophilic tendencies.
The formation of new carbon-carbon bonds employing small molecules as building blocks is crucial in organic synthesis and free radical chemistry has provided viable methods for such carbon-carbon chain extensions.2" The intermolecular addition of radicals to alkenes remains an important and versatile procedure even though problems can be associated with radical reactivity and selectivityP.4 Alkyl radicals are generally
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Regio-and stereocontrolled synthesis of vinylstannanes was achieved by intermolecular addition reaction of a~-alkoxycarbonyl-fl-stannylvinyl radicals to activated alkenes. Under high dilution conditions cyclohexene derivatives were obtained via [2+2+2] radical annulation reaction.