Assembly of C-Alkyl Glycosides by Pd/NBE-Catalyzed 1,2-Functionalization of Glycals
Penggang Zhao1, Qirui Yin1, Muhammad Nasir Siddique1
1Department State Key Laboratory of Applied Organic Chemistry, Department of Chemistry Institution, Lanzhou University, Lanzhou 730000, PR China.
Abstract:
C-alkyl glycosides constitute essential structural motifs in bioactive natural products and pharmaceutical compounds; however, their efficient synthesis continues to present substantial challenges. Herein, we describe a Catellani-reaction-enabled approach that overcomes traditional synthetic limitations, facilitating the direct and regioselective assembly of C-alkyl glycosides from alkyl halides. Our results establish the efficacy of the Catellani reaction for C-alkyl glycoside synthesis from alkyl halide precursors. Notably, this protocol displays exceptional functional group tolerance across diverse substrates while maintaining perfect regiocontrol, representing a significant advancement in Catellani reaction applications for C-glycoside construction.
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