Chemo- and regioselective ring-opening of donor-acceptor oxiranes with N-heteroaromatics.
Ji-Wei SangMing-Sheng XieMan-Man WangGui-Rong QuHai-Ming GuoPublished in: Chemical communications (Cambridge, England) (2021)
The first ring-opening of D-A oxiranes with N-heteroaromatics in a chemoselective C-C bond cleavage manner was achieved. In the presence of 5 mol% of Y(OTf)3 as the catalyst, diverse N-heteroaromatics, including benzotriazoles, purines, substituted benzimidazole, imidazole and pyrazole, reacted well with various D-A oxiranes, providing acyclic nucleoside analogues containing a N-glycosidic bond in up to 97% yield and up to >95 : 5 regioselectivity. Through simple transformation, the Ganciclovir analogue could also be obtained.
Keyphrases
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