5343-98-6Relevant articles and documents
Extending the Synthetic Utilities of the Tandem Cyclic Sulfate Rearrangement—Opening Process: Synthesis of β-Hydroxy-γ-phenyl-γ-lactam
Lee, Nagum,Yu, Min Lee,Jun, Hyeyeon,Ko, Soo Y.
, p. 2091 - 2093 (2016)
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Metal-free enaminone C-N bond cyanation for the stereoselective synthesis of (E)- And (Z)-β-cyano enones
Liu, Ting,Liu, Yunyun,Wan, Jie-Ping
supporting information, p. 9112 - 9115 (2021/09/14)
A highly practical method for C-CN bond formation by C-N bond cleavage on enaminones leading to the efficient synthesis of β-cyano enones is developed. The reactions take place efficiently to provide (E)-β-cyano enones with only a molecular iodine catalyst. In addition, the additional employment of oxalic acid enables the selective synthesis of (Z)-β-cyano enones.
A Photochemical Organocatalytic Strategy for the α-Alkylation of Ketones by using Radicals
Goti, Giulio,Melchiorre, Paolo,O?eka, Maksim,Schweitzer-Chaput, Bertrand,Spinnato, Davide
supporting information, p. 9485 - 9490 (2020/04/09)
Reported herein is a visible-light-mediated radical approach to the α-alkylation of ketones. This method exploits the ability of a nucleophilic organocatalyst to generate radicals upon SN2-based activation of alkyl halides and blue light irradiation. The resulting open-shell intermediates are then intercepted by weakly nucleophilic silyl enol ethers, which would be unable to directly attack the alkyl halides through a traditional two-electron path. The mild reaction conditions allowed functionalization of the α position of ketones with functional groups that are not compatible with classical anionic strategies. In addition, the redox-neutral nature of this process makes it compatible with a cinchona-based primary amine catalyst, which was used to develop a rare example of enantioselective organocatalytic radical α-alkylation of ketones.
