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Catalytic Asymmetric Protonation of Silyl Ketene Imines

Joyram Guin, Georgy Varseev and Benjamin List*

*Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany, Email:

J. Guin, G. Varseev, B. List, J. Am. Chem. Soc., 2013, 135, 2100-2103.

DOI: 10.1021/ja312141b

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An efficient catalytic and highly enantioselective protonation of silyl ketene imines 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. Various substituted racemic silyl ketene imines have been transformed into highly enantioenriched nitriles.

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Key Words

Nitriles, Organocatalysis

ID: J48-Y2013-0310