Organocatalytic Glycosylation by Using Electron- Deficient Pyridinium Salts
Organocatalytic Glycosylation by Using Electron- Deficient Pyridinium Salts
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DOI：
10.1002/anie.201503156
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发表时间：
2015-10-12
影响因子：
16.6
通讯作者：
Berkessel, Albrecht
中科院分区：
文献类型：
--
作者：
Das, Somnath;Pekel, Daniel;Berkessel, Albrecht
报道了一种基于缺电子吡啶盐的新型有机催化糖基化方法。在环境温度和低至 1 mol% 的催化剂负载量下，由苄基和甲硅烷基保护的糖醛以及一级或二级糖基受体形成 2-脱氧糖苷，具有优异的产率和异头选择性。机理研究表明醇-吡啶鎓缀合物（1,2-加成产物）是催化循环中的关键中间体。
A new organocatalytic glycosylation method based on electron-deficient pyridinium salts is reported. At ambient temperature and catalyst loadings as low as 1 mol%, 2-deoxyglycosides were formed from benzyl-and silyl-protected glycals and primary or secondary glycosyl acceptors, with excellent yields and anomeric selectivity. Mechanistic investigations point to alcohol-pyridinium conjugates (1,2-addition products) as key intermediates in the catalytic cycle.