Chiral induction in aryl radical cyclisations
โ Scribed by Keith Jones; Clive McCarthy
- Publisher
- Elsevier Science
- Year
- 1989
- Tongue
- French
- Weight
- 242 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
Ortho-haloacryloylanilides
carrying chiral auxiliaries on the nitrogen undergo radical cyclisation to give oxindoles in optical yields up to 39%.
We have recently described the synthesis of 3-substituted, 3,3_disubstituted, and 3,3spirooxindoles via cyclisation of the aryl radicals derived from o-bromoacryloylanilidesl.
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Amidyl radicals generated from tributylstannane mediated homolysis of O-benzoyl hydroxamic acid derivatives undergo 5-exo cyclisation to give mixtures of cis and trans pyrrolidinones. While the steric nature of the nitrogen substituents investigated had little effect on the diastereoselectivity of t
## Regiochemical and stereochemical evidence is presented which indicates that cobalt-mediated aryl radical cyclisations involve simple free radicals. Radical cyclisatton reactions have achieved considerable importance in synthetic chemistry'.
Abstmct: A synthesis of the te&ahydrofuro[2,3-blindole (3) in 6 step from 4-methoxyaniline involving a key cobalt-mediated aryl radical cycliin is presented. This hetuucycle is a known, late intermediate. in the synthesis of the alkaloid physovenine (2).