Efficient Synthesis of Dimeric Oxazoles, Piperidines and Tetrahydroisoquinolines from N-Substituted 2-Oxazolones
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- 作者：Prof. Dr. Yun He ; Dr. Piyush K. Agarwal ; Dr. I. N. Chaithanya Kiran ; Ruocheng Yu ; Bei Cao ; Cheng Zou ; Xinghua Zhou ; Huacheng Xu ; Biao Xu ; Lei Zhu ; Prof. Dr. Yu Lan and Prof. Dr. K. C. Nicolaou
- 刊名：Chemistry - A European Journal
- 出版年：2016
- 出版时间：June 1, 2016
- 年：2016
- 卷：22
- 期：23
- 页码：7696-7701
- 全文大小：2515K
- ISSN：1521-3765
文摘
A mild and practical method for the construction of heterocycles from N-substituted 2-oxazolones through cascade, BF3⋅Et2O/H2O-catalyzed reactions involving iminium ion generation and trapping by external or internal olefinic and aryl moieties is described. Mechanistic and computational studies revealed the strong protic acid HBF4 as the initiating catalyst for these cascade reactions. Providing access to novel molecular diversity, these processes may facilitate chemical biology studies, drug discovery efforts and natural products synthesis.