120312-71-2Relevant academic research and scientific papers
Gold(I)-Catalyzed Synthesis of Highly Substituted 1,4-Dicarbonyl Derivatives via Sulfonium [3,3]-Sigmatropic Rearrangement
Zhou, Weiping,Voituriez, Arnaud
supporting information, p. 247 - 252 (2021/01/09)
An efficient and straightforward gold-catalyzed protocol for the synthesis of 2-substituted 4-oxo-4-arylbutanal derivatives from commercially available or easily accessible alkynes and vinylsulfoxide substrates has been developed. Extension of the methodology to the use of 1-cycloalkenyl sulfoxides allowed the facile synthesis of five-, six-, and seven-membered-ring cycloalkyl-1-one backbone. Subsequently, the tetrahydrocycloalkyl[b]pyrrole derivatives, which are found in many active pharmaceutical ingredients, were isolated in good yields. Mechanistic investigation highlighted a [3,3]-sigmatropic rearrangement of a sulfonium intermediate in this process.
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
Carbon-Carbon Bond Formation in Reactions of PhIO*HBF4/Silyl Enol Ether Adduct with Alkenes or Silyl Enol Ethers
Zhdankin, Viktor V.,Mullikin, Michelle,Tykwinski, Rik,Berglund, Bruce,Caple, Ronald,et al.
, p. 2605 - 2608 (2007/10/02)
A new method for generation of reactive α-ketomethyl aryliodonium intermediates from silyl enol ethers and PhIO*HBF4 has been developed.Reactions of PhIO*HBF4/silyl enol ether adduct with alkenes (1-hexene, cyclohexene, α-methylstyrene, allyltrimethylsilane, 2,3-dimethyl-2-butene) yielded products of allylic alkylation or (in case of 2,3-dimethyl-2-butene) a substituted dihydrofuran.Reactions of adducts from PhIO/HBF4 and silyl enol ethers of acetophone, p-chloroacetophenone, p-methylacetophenone, and p-nitroacetophenone with various silyl enol ethers led to unsymmetrical 1,4-butanediones as major products.
