ol7b02780_si_001.pdf (2.22 MB)
Formation of Ketenimines via the Palladium-Catalyzed Decarboxylative π‑Allylic Rearrangement of N‑Alloc Ynamides
journal contribution
posted on 2017-10-20, 02:29 authored by Juliana
R. Alexander, Matthew J. CookA new approach for
the formation of ketenimines via a decarboxylative
allylic rearrangement pathway that does not require strong stabilizing
or protecting groups has been developed. The products can be readily
hydrolyzed into their corresponding secondary amides or reacted with
sulfur ylides to perform an additional [2,3]-Wittig process. Mechanistic
studies suggest an outer-sphere process in which reductive alkylation
is rate-limiting.