1244030-61-2Relevant academic research and scientific papers
Retrosynthetic Analysis of α-Alkenyl-β-Diketones: Regio-and Stereoselective Two-Step Synthesis of Highly Arylated Representatives from Acetylenes, Ketones, and Acyl Chlorides
Shabalin, Dmitrii A.,Ivanova, Elena V.,Ushakov, Igor' A.,Schmidt, Elena Yu.,Trofimov, Boris A.
, p. 8429 - 8436 (2020)
Highly arylated α-alkenyl-β-diketones are synthesized via a two-step sequence consisting of (i) potassium tert-butoxide/DMSO-catalyzed (E)-stereoselective C-H functionalization of ketones with acetylenes followed by (ii) magnesium bromide etherate/DIPEA-soft enolization of the formed β,γ-unsaturated ketones and regioselective acylation with acyl chlorides. The method is compatible with a broad range of substrates and shown to be applicable as an intermediate stage in the construction of polyarylated heterocycles.
Regio- and Stereoselective Cascade of β,γ-Unsaturated Ketones by Dipeptided Phosphonium Salt Catalysis: Stereospecific Construction of Dihydrofuro-Fused [2,3-b] Skeletons
Chen, Yayun,He, Jiajia,Jiang, Chunhui,Ren, Xiaoyu,Su, Zhishan,Wang, Tianli,Xiao, Kai,Zhang, Hongkui,Zhuang, Cheng
supporting information, p. 19860 - 19870 (2021/08/06)
Chiral (dihydro)furo-fused heterocycles are significant structural motifs in numerous natural products, functional materials and pharmaceuticals. Therefore, developing efficient methods for preparing compounds with these privileged scaffolds is an important endeavor in synthetic chemistry. Herein, we develop an effective, modular method by a dipeptide-phosphonium salt-catalyzed regio- and stereoselective cascade reaction of readily available linear β,γ-unsaturated ketones with aromatic alkenes, affording a wide variety of structurally fused heterocyclic molecules in high yields with excellent stereoselectivities. Moreover, mechanistic investigations revealed that the bifunctional phosphonium salt controlled the regio- and stereoselectivities of this cascade reaction, particularly proceeding through the initial ketone α-addition followed by O-participated substitution; and the multiple hydrogen-bonding interactions between Br?nsted acid moieties of catalyst and nitro group of aromatic alkene were crucial in asymmetric induction. Given the generality, versatility, and high efficiency of this method, we anticipate that it will have broad synthetic utilities.
A sequential synthesis of substituted furans from aryl alkynes and ketones involving a cerium(IV) ammonium nitrate (CAN)-mediated oxidative cyclization
Undeela, Sridhar,Ramchandra, Joshi P.,Menon, Rajeev S.
supporting information, p. 5667 - 5670 (2014/12/12)
A convenient, two-step synthesis of substituted furans from readily available aryl alkynes and ketones is reported. The furan-forming oxidative cyclization is mediated by the combination of cerium(IV) ammonium nitrate and potassium bromide and can be carried out in an open flask.
A one-pot approach to Δ2-isoxazolines from ketones and arylacetylenes
Schmidt, Elena Yu.,Tatarinova, Inna V.,Ivanova, Elena V.,Zorina, Nadezhda V.,Ushakov, Igor A.,Trofimov, Boris A.
supporting information, p. 104 - 107 (2013/03/28)
The sequential reaction of ketones with arylacetylenes and hydroxylamine in the presence of KOBut/DMSO followed by the treatment of the reaction mixture with H2O and KOH leads to Δ2-isoxazolines in up to 88% yield.
Base-catalyzed stereoselective vinylation of ketones with arylacetylenes: A new C(sp3)-C(sp2) bond-forming reaction
Trofimov, Boris A.,Schmidt, Elena Yu,Ushakov, IgoR'A,Zorina, Nadezhda V.,Skital'Tseva, Elena V.,Protsuk, Nadezhda I.,Mikhaleva, AL'Bina I.
supporting information; experimental part, p. 8516 - 8521 (2010/09/05)
Alkylaryl- and alkylheteroarylketones, including those with condensed aromatic moieties, are readily vinylated with arylacetylenes (KOH/DMSO, 100°C, 1 h) to give regio- and stereoselectively the (E)-β-γ- ethylenic ketones ((E)-3-buten-1-ones) in 61-84% yi
