通过糖基自由基加成和芳基迁移实现可见光介导的α-烷基糖苷的合成。
Visible-Light-Mediated Synthesis of -Alkyl Glycosides via Glycosyl Radical Addition and Aryl Migration.
作者信息
Jiao Rui-Qiang, Ding Ya-Nan, Li Ming, Shi Wei-Yu, Chen Xi, Zhang Zhe, Wei Wan-Xu, Li Xue-Song, Gong Xiao-Ping, Luan Yu-Yong, Liu Xue-Yuan, Liang Yong-Min
机构信息
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China.
College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, China.
出版信息
Org Lett. 2023 Aug 25;25(33):6099-6104. doi: 10.1021/acs.orglett.3c01988. Epub 2023 Aug 14.
A visible-light-induced glycoarylation of activated olefins has been accomplished. Glycosyl radicals are generated via radical transfer strategies between (TMS)SiOH and glycosyl bromides. Subsequent radical translocation and rapid 1,4-aryl migration form β-sugar amide derivatives, and eight types of sugars are compatible with this reaction. Further, the cascade reaction produced a quaternary carbon center with good functional group adaptability and high regioselectivity in mild conditions.
实现了可见光诱导的活化烯烃的糖芳基化反应。通过（三甲基硅基）硅醇与糖基溴之间的自由基转移策略生成糖基自由基。随后的自由基迁移和快速的1,4-芳基迁移形成β-糖酰胺衍生物，八种类型的糖与该反应兼容。此外，该串联反应在温和条件下产生了具有良好官能团适应性和高区域选择性的季碳中心。
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