Insertion of Glycosylidene Carbenes into Phenolic O-H Bonds for the Synthesis of O-Aryl Glycosides

被引：0
|
作者：
Zhu, Qibin [1 ,2 ]
Tian, Xinyu [1 ,2 ]
He, Gang [1 ,2 ,3 ]
机构：
[1] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
[2] Nankai Univ, Inst Elementoorgan Chem, Coll Chem, Tianjin 300071, Peoples R China
[3] Nankai Univ, Frontiers Sci Ctr New Organ Matter, Tianjin 300071, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2025年 / 90卷 / 08期
基金：
中国国家自然科学基金;
关键词：
STEREOCONTROLLED SYNTHESIS; GLYCOSYLATION; S(N)2-GLYCOSYLATION; PRECURSORS; INHIBITORS; ARYLATION; AIR;
D O I：
10.1021/acs.joc.4c02620
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We present a new strategy for the synthesis of O-aryl glycosides through the formal insertion of glycosylidene carbenes into the O-H bond of phenols. The key glycosylidene carbene intermediates were generated in situ by copper-catalyzed oxidation of bench-stable glycosylidene diaziridine precursors. This method enables the glycosylation of a variety of phenols with good yields, excellent diastereoselectivity, and chemoselectivity, providing a highly practical method for the late-stage glycosylation of complex natural products and bioactive agents.
引用
收藏
页码：3087 / 3092
页数：6
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