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Open Access Publications from the University of California

Silver-Catalyzed Enantioselective Propargylation Reactions of N-Sulfonylketimines.

  • Author(s): Osborne, Charlotte A
  • Endean, Thomas BD
  • Jarvo, Elizabeth R
  • et al.

The enantioselective silver-catalyzed propargylation of N-sulfonylketimines is described. This reaction proceeds in high yield and excellent enantiomeric ratio and is compatible with a wide variety of diaryl- and alkylketimines. Synthetic transformations of homopropargylic products via enyne ring-closing metathesis, Sonogashira cross-coupling, and reduction reactions proceed with high stereochemical fidelity. Both allenyl and propargyl borolane reagents can be used to obtain homopropargylic products, a distribution most consistent with a mechanism involving transmetalation of the silver catalyst with the borolane reagent.

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