Synthesis of oxa-aza spirobicycles by intramolecular hydrogen abstraction promoted by N-radicals in carbohydrate systems
✍ Scribed by Raimundo Freire; Angeles Martı́n; Inés Pérez-Martı́n; Ernesto Suárez
- Book ID
- 104251400
- Publisher
- Elsevier Science
- Year
- 2002
- Tongue
- French
- Weight
- 281 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The preparation of 1-oxa-6-azaspiro[4.4]nonane, 1-oxa-6-azaspiro[4.5]decane, 6-oxa-1-azaspiro[4.5]decane, and 1-oxa-7azaspiro[5.5]undecane ring systems by 1,6-and 1,7-hydrogen atom transfer promoted by phosphoramidyl radicals in carbohydrate models is described. The N-radicals are generated by reaction of dibenzyl phosphoramidate derivatives of C-glycosides with (diacetoxyiodo)benzene and iodine through an homolytic fragmentation of iodoamide intermediates.
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