Catalytic Asymmetric Protonation of Silyl Ketene Imines

Guin, Joyram; Varseev, Georgy; List, Benjamin

doi:10.1021/ja312141b

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Catalytic Asymmetric Protonation of Silyl Ketene Imines

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Guin, Joyram
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Varseev, Georgy
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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List, Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Guin, J., Varseev, G., & List, B. (2013). Catalytic Asymmetric Protonation of Silyl Ketene Imines. Journal of the American Chemical Society, 135(6), 2100-2103. doi:10.1021/ja312141b.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0014-A42B-9

Abstract

An efficient catalytic and highly enantioselective protonation of silyl ketene imines is described. The reaction is catalyzed by the chiral phosphoric acids TRIP or STRIP in the presence of a stoichiometric amount of methanol as the proton source and silyl acceptor. A variety of substituted racemic silyl ketene imines have been transformed into highly enantioenriched nitriles.