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- W2157302792 abstract "The reaction of phenyl and benzyl amidophosphates and alkyl and benzyl carbamate derivatives of aminoalditols with (diacetoxyiodo)benzene or iodosylbenzene and iodine is a mild and selective procedure for the synthesis of chiral 7-oxa-2-azabicyclo[2.2.1]heptane and 8-oxa-6-azabicyclo[3.2.1]octane ring systems under neutral conditions. This reaction can be considered to be an intramolecular N-glycosidation that goes through an intramolecular 1,5-hydrogen abstraction promoted by an N-amido radical followed by oxidation of the transient C-radical intermediate to an oxycarbenium ion. This methodology proved to be useful not only as a suitable strategy for the preparation of these bicyclic arrays but also for the selective oxidation of specific carbons of the carbohydrate skeleton, constituting a good procedure for the synthesis of protected N,O-uloses." @default.
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- W2157302792 date "2003-01-14" @default.
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- W2157302792 title "Intramolecular Hydrogen Abstraction Reaction Promoted by <i>N</i>-Radicals in Carbohydrates. Synthesis of Chiral 7-Oxa-2-azabicyclo[2.2.1]heptane and 8-Oxa-6-azabicyclo[3.2.1]octane Ring Systems" @default.
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- W2157302792 doi "https://doi.org/10.1021/jo026314h" @default.
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