Concise Report
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,
Xiaodong Gu
Department of Chemistry, Hong Kong Baptist University, Kowloon, Hong Kong, China
‡These authors contributed equally to this work.
Search for more papers by this authorQingwei Du
Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong, 518055 China
‡These authors contributed equally to this work.
Search for more papers by this authorWeijian Song
Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong, 518055 China
Search for more papers by this authorCorresponding Author
Jun Joelle Wang
Department of Chemistry, Hong Kong Baptist University, Kowloon, Hong Kong, China
E-mail: [email protected]Search for more papers by this authorXiaodong Gu,
Qingwei Du,
Weijian Song,
Jun Joelle Wang,
Xiaodong Gu
Department of Chemistry, Hong Kong Baptist University, Kowloon, Hong Kong, China
‡These authors contributed equally to this work.
Search for more papers by this authorQingwei Du
Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong, 518055 China
‡These authors contributed equally to this work.
Search for more papers by this authorWeijian Song
Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong, 518055 China
Search for more papers by this authorCorresponding Author
Jun Joelle Wang
Department of Chemistry, Hong Kong Baptist University, Kowloon, Hong Kong, China
E-mail: [email protected]Search for more papers by this author†Dedicated to the Special Issue of Emerging Investigators in 2022.
Comprehensive Summary
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.
Supporting Information
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Appendix S1: Supporting Information |
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