ol5b02692_si_005.cif (517.54 kB)

Silver-Catalyzed Enantioselective Propargylation Reactions of N‑Sulfonylketimines

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posted on 06.11.2015, 00:00 by Charlotte A. Osborne, Thomas B. D. Endean, Elizabeth R. Jarvo
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.