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Chemo- and regioselective ring-opening of donor-acceptor oxiranes with N -heteroaromatics.
- Source :
-
Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2021 May 06; Vol. 57 (37), pp. 4552-4555. - Publication Year :
- 2021
-
Abstract
- 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.
Details
- Language :
- English
- ISSN :
- 1364-548X
- Volume :
- 57
- Issue :
- 37
- Database :
- MEDLINE
- Journal :
- Chemical communications (Cambridge, England)
- Publication Type :
- Academic Journal
- Accession number :
- 33956013
- Full Text :
- https://doi.org/10.1039/d1cc00600b