The Schomaker group reported a sequential Ichikawa/ Overman rearrangement strategy towards 2 in 2019; while the Ichikawa rearrangement was successful in furnishing 8 (Scheme 1) after deprotection of the C4 alcohol, the allylic trichloroacetimidate precursor for the Overman rearrangement could not be successfully prepared. Instead, the oxazoline 9 was observed as the major product; this is hypothesized to arise via reaction of the urea oxygen with trichloroacetonitrile, followed by attack of the C4 oxygen across the ring to displace trichloroacetamide. Attempts to initiate a second Ichikawa rearrangement from the carbamate of 8 resulted in an SN2' attack of the urea oxygen at C2 to give 10. Thus, we proposed that the desired rearrangement sequence to install the C1/C2 vicinal diamine motif would be most likely to be successful if the C4 group was nonnucleophilic and a poor leaving group. In addition, desired reactivity would be further aided by minimization of the electrophilicity at C2 (Scheme 1, bottom right). Scheme 1. Failed Ichikawa/Overman rearrangement.