A stereoselective organocatalyzed C-glycosylation of indole: implications of acceptor-catalyst-donor interactions - Details

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A　stereoselective　pyridinium　hexafluorophosphate-catalyzed　C-glycosylation　of　indole　is　presented,　featuring　the　plausible　formation　of　a　catalyst-acceptor　complex　and　a　crucial　H-bond　between　the　N-H　group　of　indole　and　the　oxygen　atom　at　the　C6　position　of　the　glycosyl　donor,　which　are　proposed　to　collectively　facilitate　the　glycosylation　process.　This　reaction　proceeds　under　mild　conditions,　enabling　the　selective　synthesis　of　a　wide　range　of　C-indolyl　glycosides.　©　2024　The　Royal　Society　of　Chemistry.

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[ 1 ] [Xie L.]Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, Fuzhou, 350108, China
[ 2 ] [Liu W.]Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, Fuzhou, 350108, China
[ 3 ] [Guo Z.]State Key Laboratory of Elemento-organic Chemistry, College of Chemistry, Nankai University, Weijin Road No. 94, Tianjin, 300071, China
[ 4 ] [Jiao Q.]Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, Fuzhou, 350108, China
[ 5 ] [Shen X.]Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, Fuzhou, 350108, China
[ 6 ] [Liu T.]State Key Laboratory of Elemento-organic Chemistry, College of Chemistry, Nankai University, Weijin Road No. 94, Tianjin, 300071, China
[ 7 ] [Xu C.]Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemistry, Fuzhou University, Fuzhou, 350108, China
[ 8 ] [Xu C.]Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, CAS, Shanghai, 200032, China

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Organic Chemistry Frontiers

ISSN： 2052-4110

Year： 2024

Issue： 2

Volume： 12

Page： 509-515

4 . 6 0 0

JCR@2023

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