Synthesis of Reversed C-Acyl Glycosides through Ni/Photoredox Dual Catalysis.
Synthesis of Reversed C-Acyl Glycosides through Ni/Photoredox Dual Catalysis.
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DOI：
10.1002/anie.201800701
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发表时间：
2018-05-28
期刊：
影响因子：
--
通讯作者：
Molander GA
中科院分区：
文献类型：
--
作者：
Badir SO;Dumoulin A;Matsui JK;Molander GA
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. 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.
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