Chemoselective Access to γ‑Ketoesters
with Stereogenic Quaternary α‑Center or γ‑Keto
Nitriles by Aerobic Reaction of α-Cyanoesters and Styrenes
Song-Lin Zhang
Xian-Jin Wang
Ze-Long Yu
10.1021/acs.orglett.7b01264.s001
https://acs.figshare.com/articles/journal_contribution/Chemoselective_Access_to_Ketoesters_with_Stereogenic_Quaternary_Center_or_Keto_Nitriles_by_Aerobic_Reaction_of_-Cyanoesters_and_Styrenes/5053747
Chemoselective
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.
2017-05-31 14:20:56
Styrenes Chemoselective access
quaternary all-carbon α- stereogenic center
γ- ketoesters
Aerobic Reaction
styrene
α- Cyanoesters
Formal oxo-enolation
γ- keto nitriles
Chemoselective Access
stoichiometric metal salts waste
α- cyanoesters