Electrophilic substitution of a 2-azabicyclo[2.2.1]hept-5-en-3-one as a potential route to 3-deoxycarbocyclic nucleosides

Abstract
The γ-lactam 9 reacted with bromine in the presence of acetic acid or fluoride ion to give the 6,7-substituted 2-azanorbornan-3-ones 10 or 15 respectively. The latter compounds were converted into the cyclopentylamine derivatives 14 and 16 which represent potentially useful precursors for carbocyclic 3-deoxyribonucleosides.

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