Details

Autor(en) / Beteiligte

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

Titel

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

Ist Teil von

• Angewandte Chemie International Edition, 2018-04, Vol.57 (22), p.6610-6613

Erscheinungsjahr

2018

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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, becoming an extensive topic of synthetic efforts in recent decades. [ 1 ] Described herein is a practical, scalable, and versatile route for the synthesis of non-anomeric and unexploited C -acyl glycosides via a Ni/photoredox dual catalytic system. Utilizing an organic photocatalyst, an arsenal of glycosyl-based radicals is 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. C -acyl glycosides, naturally occurring building blocks, have recently been the focus of extensive research efforts due to their enhanced biological activities and unique chemical structure. We describe a practical and versatile route toward non anomeric C -acyl glycosides via Ni/Photoredox dual catalysis. Key to this transformation is the preservation of the anomeric carbon as a handle for further late-stage derivatization. This process is operationally simple and widely applicable to various functional groups. An organic photocatalyst is utilized to generate an array of glycosyl-based radicals that engage in cross-coupling with in-situ activated carboxylic acids to access medicinally relevant compounds.