Highly Diastereoselective Synthesis of C-Glycosides from Glycal Anomers,Organic Letters

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Highly Diastereoselective Synthesis of C-Glycosides from Glycal Anomers
Organic Letters ( IF 4.9 ) Pub Date : 2023-06-05 , DOI: 10.1021/acs.orglett.3c01605
Lisi Yuan ₁ , Ya Fang ₁ , Zhaobo Zhou ₁ , Tinghong Lv ₁ , Yingpeng Su ₂ , Jian Liu ₁ , Xiaolei Wang _{1,

3}

Affiliation

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.

中文翻译：

从甘醇异头物高度非对映选择性合成 C-糖苷

这封信介绍了使用手性N -杂环卡宾 - 铜催化剂从甘醇异头物高度非对映选择性合成C -羟基次甲基糖苷。高非对映选择性受底物的立体中心和N-杂环卡宾-铜配合物的手性协同控制，而不会被 C5 的立体化学和端基异构位置打断。这种方法能够使用合成通用的糖醛和各种功能化的醛来生产各种C-羟基次甲基糖苷。

更新日期：2023-06-05

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