ol7b01264_si_001.pdf (2.29 MB)
Chemoselective Access to γ‑Ketoesters with Stereogenic Quaternary α‑Center or γ‑Keto Nitriles by Aerobic Reaction of α-Cyanoesters and Styrenes
journal contribution
posted on 2017-05-31, 14:20 authored by Song-Lin Zhang, Xian-Jin Wang, Ze-Long YuChemoselective
access to either γ-ketoesters with a quaternary
all-carbon α-stereogenic center or γ-keto nitriles is
described by copper-catalyzed aerobic reaction of styrenes with α-cyanoesters.
Formal oxo-enolation or oxo-cyanomethylation of styrenes is achieved
via a sequence of addition of enolate (or cyanomethyl) radical to
olefin and oxidation of the resulting radical adduct. This method
starts from abundant and cheap feedstock under aerobic conditions,
without any prefunctionalization or the production of stoichiometric
metal salts waste, making it very attractive for practical use.