Application of chiral cyclic nitrones to the diastereoselective synthesis of bicyclic isoxazolidine nucleoside analogues

Nucleosides, Nucleotides & Nucleic Acids
Evdoxia Coutouli-ArgyropoulouNikolaos G Argyropoulos

Abstract

New bicyclic isoxazolidine nucleoside analogues are synthesized through 1,3-dipolar cycloaddition of enantiopure cyclic nitrones to appropriate vinyl nucleobases. The reactions are diastereoselective, giving as the main or the sole product the exo-Re cycloadducts. The diastereoselectivity depends on both the kind of the base and the substitution pattern of the nitrone.

Citations

Dec 17, 2016·Chemical Reviews·Mathéo BerthetJean Martinez
Jan 20, 2009·The Journal of Organic Chemistry·Emilie RacineSandrine Py
Nov 15, 2018·The Journal of Organic Chemistry·Ekta GuptaKishor Mohanan
Aug 28, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Agnieszka Kącka-Zych

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