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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-MeOBIPHEPAu2Cl2 (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.
Zhang et al. (Tue,) studied this question.