First efficient and general copper-catalyzed [2,3]-rearrangement of tetrahydropyridinium ylids.
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]
Roberts
Edward
E
Department of Chemistry, University of Reading, Reading RG6 6AD, U.K.
Sançon
Julien P
JP
Sweeney
Joseph B
JB
Workman
James A
JA