Gold(I)-Catalyzed Dynamic Kinetic Enantioselective Intramolecular Hydroamination of Allenes

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Abstract

Treatment of benzyl 6-methyl-2,2-diphenyl-4,5-octadienyl carbamate (2a) with a catalytic 1:2 mixture of [(S)-3,5-t-Bu-4-MeO-MeOBIPHEP]Au2Cl2 [(S)-1] and AgClO4 (5 mol %) led to isolation of a 3.1:1 mixture of (R,Z)-3a and (R,E)-3a in 94% combined yield with 96 and 76% ee, respectively. Analyses of concentration versus time and/or conversion plots for the reaction of both racemic and enantiomerically enriched 2a with 1 were consistent with conversion of (R)-2a to (R,Z)-3a in the matched reaction manifold and conversion of (S)-2a to (R,E)-3a in the mismatched reaction manifold via the net anti-addition of Au and N across the internal CC bond of 2a.

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