Unstabilized Azomethine Ylides for the Stereoselective Synthesis of Substituted Piperidines, Tropanes, and Azabicyclo[3.1.0] Systems

作者:Ischay Michael A; Takase Michael K; Bergman Robert G; Ellman Jonathan A*
来源:Journal of the American Chemical Society, 2013, 135(7): 2478-2481.
DOI:10.1021/ja312311k

摘要

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-pi electrocyclization that upon reduction give 2-azabicyclo[3.1.0] systems.

  • 出版日期2013-2-20