The chemoselective reduction of isoxazoline γ-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.
Dipartimento di Chimica, Università degli Studi di Pavia, Viale Taramelli 12, 27100 Pavia, Italy.
Misal Giuseppe
MG
Memeo
Mariella
M
Mella
Paolo
P
Quadrelli
D000577:Amides / Q000737:chemistry*; D007555:Isoxazoles / Q000737:chemistry*; D007769:Lactams / Q000737:chemistry*; D009705:Nucleosides / Q000138:chemical synthesis*; D010084:Oxidation-Reduction
D000577:Amides; D007555:Isoxazoles; D007769:Lactams; D009705:Nucleosides