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

Roberts, E., Sancon, J.P., Sweeney, J.B. and Workman, J.A. (2003) First efficient and general copper-catalyzed [2,3]-rearrangement of tetrahydropyridinium ylids. Organic Letters, 5 (25). pp. 4775-4777. ISSN 1523-7060 doi: 10.1021/ol035747j

Abstract/Summary

The factors affecting the copper-catalyzed rearrangement of ammonium ylids derived from tetrahydropyriclines 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.