Chalcone-Based Pyridinium Salts and Their Diastereoselective Dearomatization To Access Bibridged Benzoazepines
Chalcone-Based Pyridinium Salts and Their Diastereoselective Dearomatization To Access Bibridged Benzoazepines
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DOI：
10.1021/acs.orglett.9b04398
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发表时间：
2020-02-07
期刊：
影响因子：
5.2
通讯作者：
Wang, Qi-Lin
中科院分区：
文献类型：
--
作者：
Wang, Le-Le;Han, Hua-Bin;Wang, Qi-Lin
新的查尔酮吡啶盐被成功地开发出来，它可以顺利地参与高度非对映选择性的脱芳构化与双核烯胺酮，利用其多个反应位点的优势，以高达89%的产率构建bibridged benzoazepines。成功的关键是新吡啶鎓盐的巧妙和前所未有的C-3官能化。本工作不仅提供了一种新型的吡啶鎓盐合成子，而且首次实现了吡啶鎓盐的C-3位功能化，以高的合成效率构建了复杂且具有挑战性的双桥苯并氮杂卓化合物。
New chalcone-based pyridinium salts have been successfully exploited, which could smoothly participate in the highly diastereoselective dearomatization with binucleophilic enaminones by taking advantage of their multiple reactive sites to construct bibridged benzoazepines in up to 89% yields. The key to the success was the skillful and unprecedented C-3 functionalization of the new pyridinium salts. This work not only provides a kind of novel pyridinium salt synthon but also achieves the first C-3 functionalization of pyridinium salts to construct complex and challenging bibridged benzoazepines with high synthetic efficiency.