Anion-Bridged Dual Hydrogen Bond Enabled Concerted Addition of Phenol to Glycal - Details

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Abstract：

A　noncovalent　organocatalytic　concerted　addition　of　phenol　to　glycal　is　developed　for　the　stereoselective　and　regioselective　construction　of　biologically　important　phenolic　2-deoxyglycosides,　featuring　wide　substrate　tolerance.　The　method　relies　on　an　anion-bridged　dual　hydrogen　bond　interaction　which　is　experimentally　proved　by　Nuclear　Magnetic　Resonance　(NMR),　Ultraviolet　and　visible　(UV–vis),　and　fluorescence　analysis.　Experimental　evidence　including　kinetic　analysis,　Kinetic　Isotope　Effect　(KIE)　studies,　linear　free　energy　relationship,　Hammett　plot,　and　density　functional　theory　(DFT)　calculations　is　provided　for　a　concerted　mechanism　where　a　high-energy　oxocarbenium　ion　is　not　formed.　In　addition,　the　potential　utility　of　this　method　is　further　demonstrated　by　the　synthesis　of　biologically　active　glycosylated　flavones.　The　benchmarking　studies　demonstrate　significant　advances　in　this　newly　developed　method　compared　to　previous　approaches.　©　2024　The　Authors.　Advanced　Science　published　by　Wiley-VCH　GmbH.

Keyword：

Density functional theory Fluorescence Free energy Hydrogen bonds Ions Nuclear magnetic resonance Phenols

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[ 1 ] [Jiao, Qinbo]Institute of Pharmaceutical Science and Technology, College of Chemistry, Fuzhou University, Fuzhou; 350108, China
[ 2 ] [Guo, Zhenbo]State Key Laboratory of Elemento-organic Chemistry, College of Chemistry, Nankai University, Weijin Road No. 94, Tianjin; 300071, China
[ 3 ] [Guo, Zhenbo]Haihe Laboratory of Sustainable Chemical Transformations, Tianjin; 300192, China
[ 4 ] [Zheng, Mingwen]Institute of Pharmaceutical Science and Technology, College of Chemistry, Fuzhou University, Fuzhou; 350108, China
[ 5 ] [Lin, Wentao]Institute of Pharmaceutical Science and Technology, College of Chemistry, Fuzhou University, Fuzhou; 350108, China
[ 6 ] [Liao, Yujie]Institute of Pharmaceutical Science and Technology, College of Chemistry, Fuzhou University, Fuzhou; 350108, China
[ 7 ] [Yan, Weitao]Institute of Pharmaceutical Science and Technology, College of Chemistry, Fuzhou University, Fuzhou; 350108, China
[ 8 ] [Liu, Tianfei]State Key Laboratory of Elemento-organic Chemistry, College of Chemistry, Nankai University, Weijin Road No. 94, Tianjin; 300071, China
[ 9 ] [Xu, Chunfa]Institute of Pharmaceutical Science and Technology, College of Chemistry, Fuzhou University, Fuzhou; 350108, China
[ 10 ] [Xu, Chunfa]Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai; 200032, China

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Advanced Science

Year： 2024

Issue： 11

Volume： 11

1 4 . 3 0 0

JCR@2023

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