Heath, Peter, Roberts, Edward, Sweeney, Joseph B., Wessel, Hans Peter and Workman, James A. (2003) Copper(II)-Catalyzed [2,3]-Sigmatropic Rearrangement ofN-Methyltetrahydropyridinium Ylids. The Journal of Organic Chemistry, 68 (10). pp. 4083-4086. ISSN 0022-3263
Abstract

A ring-contractive and highly diastereoselective [2,3]-sigmatropic rearrangement occurs when N-methyl-1,2,3,6-tetrahydropyridine is treated with sub-stoichiometric amounts of copper or rhodium salts, in the presence of ethyl diazoacetate, giving ethyl cis-N-methyl-3-ethenyl proline (4).

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