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- Title
Synthesis of Reversed C‐Acyl Glycosides through Ni/Photoredox Dual Catalysis.
- Authors
Badir, Shorouk O.; Dumoulin, Audrey; Matsui, Jennifer K.; Molander, Gary A.
- Abstract
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.
- Subjects
GLYCOSIDE synthesis; ACYL group; NICKEL catalysts; PHOTOCATALYSIS; DRUG design
- Publication
Angewandte Chemie, 2018, Vol 130, Issue 22, p6720
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201800701