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Chiral sulfinamide/achiral sulfonic acid cocatalyzed enantioselective protonation of enol silanes.

Organic letters (2011-07-27)
Elizabeth M Beck, Alan M Hyde, Eric N Jacobsen
RÉSUMÉ

The application of chiral sulfinamides and achiral sulfonic acids as a cocatalyst system for enantioselective protonation reactions is described. Structurally simple, easily accessible sulfinamides were found to induce moderate-to-high ee's in the formation of 2-aryl-substituted cycloalkanones from the corresponding trimethylsilyl enol ethers.

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Sigma-Aldrich
(R)-N-[(1R,2R)-2-(3-(3,5-Bis(trifluoromethyl)phenyl)ureido)cyclohexyl]-tert-butyl-sulfinamide, 96%