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Silver-Catalyzed Enantioselective Propargylation Reactions of N-Sulfonylketimines.

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

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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