54669-76-0Relevant articles and documents
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.
The synthesis of cycloalka[: B] furans via an Au(i)-catalyzed tandem reaction of 3-yne-1,2-diols
Liu, Wei-Ting,Xu, Zheng-Liang,Mou, Xue-Qing,Zhang, Bang-Hong,Bao, Wen,Wang, Shao-Hua,Lee, Dongjun,Lei, Lin-Sheng,Zhang, Kun
supporting information, p. 6333 - 6337 (2017/08/10)
An Au(i)-catalyzed cyclization/1,2-rearrangement/aromatization cascade of 3-yne-1,2-diols has been successfully realized. This reaction not only provides a new and efficient strategy for the synthesis of substituted cycloalka[b]furan compounds as well as their derivatives, but might also facilitate related biological studies.
Catalyst-free formation of 1,4-diketones by addition of silyl enolates to oxyallyl zwitterions in situ generated from α-haloketones
Luo, Juan,Jiang, Qihua,Chen, Hao,Tang, Qiang
, p. 67901 - 67908 (2015/08/24)
Reported here is the exclusive formation of 1,4-diketones by the uncatalyzed reaction of silyl enolates and α-haloketones. Enolates I are inherently more likely to react with α-haloketones II at the carbonyl carbon to produce halohydrin derivatives III or