Synthesis of Reversed C-Acyl Glycosides through Ni/Photoredox Dual Catalysis

Shorouk O. Badir, Audrey Dumoulin, Jennifer K. Matsui, Gary A. Molander

Research output: Contribution to journalArticlepeer-review

95 Scopus citations

Abstract

The incorporation of C-glycosides in drug design has become a routine practice for medicinal chemists. These naturally occurring building blocks exhibit attractive pharmaceutical profiles, and have become an important target of synthetic efforts in recent decades. Described herein is a practical, scalable, and versatile route for the synthesis of non-anomeric and unexploited C-acyl glycosides through a Ni/photoredox dual catalytic system. By utilizing an organic photocatalyst, a range of glycosyl-based radicals are generated and efficiently coupled with highly functionalized carboxylic acids at room temperature. Distinctive features of this transformation include its mild conditions, impressive compatibility with a wide array of functional groups, and most significantly, preservation of the anomeric carbon: a handle for further, late-stage derivatization.

Original languageEnglish
Pages (from-to)6610-6613
Number of pages4
JournalAngewandte Chemie - International Edition
Volume57
Issue number22
DOIs
StatePublished - 28 May 2018
Externally publishedYes

Keywords

  • 1,4-dihydropyridines
  • acylation
  • carboxylic acids
  • glycosides
  • single-electron transfer

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