Abe Reiji, Nagao Kazunori, Seki Tomohiro, Hata Dai, Sasaki Yusuke, Ohmiya Hirohisa
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan.
Research, Takeda Pharmaceutical Company Limited, Fujisawa, Kanagawa 251-8555, Japan.
Org Lett. 2025 Jan 24;27(3):795-801. doi: 10.1021/acs.orglett.4c04439. Epub 2025 Jan 13.
4'-Selective alkylation of nucleosides has been recognized as one of the ideal and straightforward approaches to chemically modified nucleosides, but such a transformation has been scarce and less explored. In this Letter, we combine a visible-light-mediated photoredox catalysis and hydrogen atom transfer (HAT) auxiliary to achieve β-C(sp)-H alkylation of alcohol on tetrahydrofurfuryl alcohol scaffolds and exploit it for 4'-selective alkylation of nucleosides. The reaction involves an intramolecular 1,5-HAT process and stereocontrolled Giese addition of the resultant radicals.
核苷的4'-选择性烷基化已被认为是化学修饰核苷的理想且直接的方法之一，但这种转化很少见且研究较少。在本通讯中，我们结合可见光介导的光氧化还原催化和氢原子转移（HAT）助剂，实现了四氢糠醇支架上醇的β-C(sp)-H烷基化，并将其用于核苷的4'-选择性烷基化。该反应涉及分子内1,5-HAT过程和所得自由基的立体控制吉泽加成反应。
Zotero 插件
