Copper(II)-catalyzed [2,3]-sigmatropic rearrangement of N-methyltetrahydropyridinium ylids

  • Heath, P.
  • Roberts, E.
  • Sweeney, J.B.
  • Wessel, H.P.
  • Workman, J.A.
Publication date
January 2003
Publisher
American Chemical Society (ACS)
ISSN
0022-3263
Citation count (estimate)
16

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)

Extracted data

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