Unstabilized Azomethine Ylides for the Stereoselective Synthesis of Substituted Piperidines, Tropanes, and Azabicyclo[3.1.0] Systems
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- 作者：Michael A. Ischay ; Michael K. Takase ; Robert G. Bergman ; Jonathan A. Ellman
- 刊名：The Journal of the American Chemical Society
- 出版年：2013
- 出版时间：February 20, 2013
- 年：2013
- 卷：135
- 期：7
- 页码：2478-2481
- 全文大小：387K
- 年卷期：v.135,no.7(February 20, 2013)
- ISSN：1520-5126
文摘
Acid treatment of densely substituted 2-silyl-1,2-dihydropyridines provides a new and convenient entry to reactive azomethine ylides that can (1) be protonated and reduced with high stereoselectivity to give piperidines, (2) participate in [3 + 2] dipolar cycloaddition to give tropanes, and (3) undergo a Nazarov-like 6-蟺 electrocyclization that upon reduction give 2-azabicyclo[3.1.0] systems.