TMSOTf mediated stereoselective synthesis of α-C-glycosides from unactivated aryl acetylenes

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• 作者：Heshan Chen ; Xiaosheng Luo ; Saifeng Qiu ; Wengjie Sun…
• 关键词：Metal free ; C ; glycosides ; TMSOTf ; Aryl acetylenes ; Glycals
• 刊名：Glycoconjugate Journal
• 出版年：2017
• 出版时间：February 2017
• 年：2017
• 卷：34
• 期：1
• 页码：13-20
• 全文大小：
• 刊物类别：Biomedical and Life Sciences
• 刊物主题：Biochemistry, general; Pathology;
• 出版者：Springer US
• ISSN：1573-4986
• 卷排序：34

文摘

A metal free and highly stereoselective procedure for the synthesis of 2,3-unsaturated-C-glycosides has been developed between glycals and unactivated aryl acetylenes in the presence of TMSOTf through a triflated C-vinyl glycosides intermediate. The flexibility of the procedure was tested by a wide variety of glycals and unactivated aryl acetylenes (20 examples). The corresponding alkynyl C-glycosides were obtained in good yields with completely α-selectivity in a short time (<25 min). And a plausible mechanism for the synthesis of alkynyl C-glycosides was depicted.