Silver-Catalyzed Enantioselective Propargylation Reactions of N-Sulfonylketimines
- Author(s): Osborne, CA
- Endean, TBD
- Jarvo, ER
- et al.
Published Web Locationhttps://doi.org/10.1021/acs.orglett.5b02692
© 2015 American Chemical Society. 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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