Catalytic asymmetric protonation of silyl ketene imines.
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.
Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany.
Joyram
J
Guin
Georgy
G
Varseev
Benjamin
B
List
D002384:Catalysis; D005030:Ethylenes / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry; D017646:Organosilicon Compounds / Q000737:chemistry*; D011522:Protons; D013237:Stereoisomerism
D005030:Ethylenes; D007097:Imines; D007659:Ketones; D009570:Nitriles; D017646:Organosilicon Compounds; D011522:Protons; C008223:ketene