Isoxazoline γ-lactams are prepared starting from the regioisomeric cycloadducts of benzonitrile oxide to the N-alkyl 2- azanorbornenes taking advantage of the efficient catalytic oxidation by RuO4. The reduction of the amide groups is easily conducted in the presence of LiAlH4 under mild conditions, which allowed for the chemoselective reduction of the amide moiety followed by ring opening to afford the desired conformationally locked isoxazoline-carbocyclic aminols, as valuable intermediates for nucleoside synthesis.

The Chemoselective Reduction of Isoxazoline γ-LactamsThrough Iminium Aza-Diels-Alder Reactions: A Short-CutSynthesis of Aminols as Valuable Intermediates towardsNucleoside Derivatives

MEMEO, MISAL GIUSEPPE;MELLA, MARIELLA;QUADRELLI, PAOLO
2012

Abstract

Isoxazoline γ-lactams are prepared starting from the regioisomeric cycloadducts of benzonitrile oxide to the N-alkyl 2- azanorbornenes taking advantage of the efficient catalytic oxidation by RuO4. The reduction of the amide groups is easily conducted in the presence of LiAlH4 under mild conditions, which allowed for the chemoselective reduction of the amide moiety followed by ring opening to afford the desired conformationally locked isoxazoline-carbocyclic aminols, as valuable intermediates for nucleoside synthesis.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11571/413532
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