Catalyst-free Regio- and Diastereoselective Synthesis of Heterocyclic Nucleosides in the Eco-friendly Solvent 2-Methyltetrahydrofuran

Xiaodong Gu, Qingwei Du, Weijian Song, Jun (Joelle) Wang*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

An efficient and practical synthesis of heterocyclic nucleosides is developed by a catalyst-free highly regioselective and diastereoselective [3+2] annulation of α-purine-substituted acrylates with nitrones. The reaction operates with excellent functional group tolerance, very mild reaction conditions, and with the green, sustainable, and eco-friendly 2-methyltetrahydrofuran (2-MeTHF) as solvent. Compared with other reactions of electron-deficient olefin dipolarophiles with nitrones, different regioselective cycloaddition products were observed in this work. This 1,3-dipolar cycloaddition reaction gives a series of isoxazolidinyl nucleosides in good to excellent yields with promising applications in biochemistry and medicinal chemistry.
Original languageEnglish
JournalChinese Journal of Chemistry
DOIs
Publication statusE-pub ahead of print - 10 Oct 2022

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