Chalcone-Based Pyridinium Salts and Their Diastereoselective Dearomatization To Access Bibridged Benzoazepines
Lele Wang, Huabin Han, Zhaohui Cui, Junwei Zhao, Zhanwei Bu, Qilin Wang
Abstract
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.
Topics & Concepts
PyridiniumSynthonChemistryChalconeSalt (chemistry)Surface modificationCombinatorial chemistryPyridinium CompoundsOrganic chemistryPhysical chemistryAxial and Atropisomeric Chirality SynthesisCatalytic C–H Functionalization MethodsAlkaloids: synthesis and pharmacology