Silver-Catalyzed Enantioselective Propargylation Reactions of N-Sulfonylketimines.
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.
Department of Chemistry, University of California , Irvine, California 92697, United States.
Charlotte A
CA
Osborne
Department of Chemistry, University of California , Irvine, California 92697, United States.
Thomas B D
TB
Endean
Department of Chemistry, University of California , Irvine, California 92697, United States.
Elizabeth R
ER
Jarvo
D001896:Boron Compounds / Q000737:chemistry; D002384:Catalysis; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D010293:Pargyline / Q000737:chemistry; D012834:Silver / Q000737:chemistry*; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*
D001896:Boron Compounds; D007097:Imines; D009570:Nitriles; D013450:Sulfones; C542835:ketimine; D012834:Silver; D010293:Pargyline