The Chemoselective Reduction of Isoxazolineγ-Lactams Through Iminium Aza-Diels-Alder Reactions: A Short-Cut Synthesis of Aminols as Valuable Intermediates towards Nucleoside Derivatives

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 RuO 4 . The reduction of the amide groups is easily conducted in the presence of LiAlH 4 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.