Silver-Catalyzed Enantioselective Propargylation Reactions of N-Sulfonylketimines.
- Author(s): Osborne, Charlotte A;
- Endean, Thomas BD;
- Jarvo, Elizabeth R
- et al.
Published Web Locationhttps://doi.org/10.1021/acs.orglett.5b02692
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.