Highly Diastereoselective Synthesis of C-Glycosides from Glycal Anomers.

This Letter presents a highly diastereoselective synthesis of C-hydroxymethine glycosides from glycal anomers using a chiral N-heterocyclic carbene-copper catalyst. The high diastereoselectivity was synergistically controlled by the stereocenter of the substrate and chirality of the N-heterocyclic carbene-copper complex without being interrupted by the stereochemistry of C5 and the anomeric position. This approach enables the production of a diverse array of C-hydroxymethine glycosides using synthetically versatile glycals and various functionalized aldehydes.

Citation

Lisi Yuan, Ya Fang, Zhaobo Zhou, Tinghong Lv, Yingpeng Su, Jian Liu, Xiaolei Wang. Highly Diastereoselective Synthesis of C-Glycosides from Glycal Anomers. Organic letters. 2023 Jun 16;25(23):4394-4399

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PMID: 37272658

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