First efficient and general copper-catalyzed [2,3]-rearrangement of tetrahydropyridinium ylids

Academic Article
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publication date

  • December 2003

abstract

  • The factors affecting the copper-catalyzed rearrangement of ammonium ylids derived from tetrahydropyridines and diazoesters have been examined,and the first examples of high-yielding metal-catalyzed [2,3]-sigmatropic rearrangements of a wide range of such ylids are reported. The nature of the alpha-substituent in the diazo component of the reaction has a dramatic effect upon the yields of the reaction, with electron-withdrawing substituents enhancing the yield of the reaction. [reaction: see text]