27729-96-0Relevant academic research and scientific papers
Asymmetric Epoxidation of Enones Promoted by Dinuclear Magnesium Catalyst
Jaszczewska-Adamczak, Joanna A.,Mlynarski, Jacek
supporting information, p. 4247 - 4255 (2021/07/17)
Asymmetric synthesis with cheaper and non-toxic alkaline earth metal catalysts is becoming an important and sustainable alternative to conventional catalytic methodologies mostly relying on precious metals. In spite of some sustainable methods for enantioselective epoxidation of enones, the development of a well-defined and efficient catalyst based on magnesium complexes for these reactions is still a challenging task. In this perspective, we present the application of chiral dinuclear magnesium complexes for asymmetric epoxidation of a broad range of electron-deficient enones. We demonstrate that the in situ generated magnesium-ProPhenol complex affords enantioenriched oxiranes in high yields and with excellent enantioselectivities (up to 99% ee). Our extensive study verifies the literature data in this area and provides a step forward to better understand the factors controlling the oxygenation process. Elaborated catalyst offers mild reaction conditions and a truly wide substrate scope. (Figure presented.).
Peroxide- And transition metal-free electrochemical synthesis of α,β-epoxy ketones
Zhang, Mengxun,Chen, Tie,Fang, Shisong,Wu, Weihua,Wang, Xin,Wu, Haiqiang,Xiong, Yongai,Song, Jun,Li, Chenyang,He, Zhendan,Lee, Chi-Sing
supporting information, p. 2481 - 2486 (2021/04/02)
A novel electrochemical method for the synthesis of α,β-epoxy ketones is reported. With KI as the redox mediator, methyl ketones reacted with aldehydes under peroxide- and transition metal-free electrolytic conditions and afforded α,β-epoxy ketones in one pot (36 examples, 52-90% yield). This safe and environmental-friendly method has a broad substrate scope and can readily provide a variety of α,β-epoxy ketones in gram-scales for evaluation of their anti-cancer activities.
Organocatalytic Enantioselective γ-Elimination: Applications in the Preparation of Chiral Peroxides and Epoxides
Chen, Zhili,Gong, Xiangnan,Hu, Fangli,Huang, Shengli,Jia, Shiqi,Qin, Wenling,Tan, Yu,Xu, Da,Yan, Hailong
, p. 1934 - 1940 (2020/03/24)
An organocatalyzed enantioselective γ-elimination process has been achieved and applied in the kinetic resolution of peroxides to access chiral peroxides and epoxides. The reaction provided a pathway for the preparation of two useful synthetic and biologically important structural motifs through a single-step reaction. A range of substrates has been resolved with a selectivity factor up to 63. The obtained enantioenriched peroxides and epoxides allowed a series of transformations with retained optical purities.
Highly Enantioselective Epoxidation of α,β-Unsaturated Ketones Using Amide-Based Cinchona Alkaloids as Hybrid Phase-Transfer Catalysts
Jurczak, Janusz,Majdecki, Maciej,Tyszka-Gumkowska, Agata
, (2020/11/13)
A series of 20 one chiral epoxides were obtained with excellent yields (up to 99%) and enantioselectivities (up to >99% ee) using hybrid amide-based Cinchona alkaloids. Our method is characterized by low catalyst loading (0.5 mol %) and short reaction times. Moreover, the epoxidation process can be carried out in 10 cycles, without further catalyst addition to the reaction mixture. This methodology significantly enhance the scale of the process using very low catalyst loading.
Lanthanide complexes combined with chiral salen ligands: Application in the enantioselective epoxidation reaction of α,β-unsaturated ketones
Xia, Xuexiu,Lu, Chengrong,Zhao, Bei,Yao, Yingming
, p. 13749 - 13756 (2019/05/16)
Readily available lanthanide amides Ln[N(SiMe3)2]3 (Ln = Nd (1), Sm (2), Eu (3), Yb (4), La (5)), combined with chiral salen ligands H2La ((S,S)-N,N′-di-(3,5-disubstituted-salicylidene)-1,2-cyclohexan
Visible Light-Induced Aerobic Epoxidation of α,β-Unsaturated Ketones Mediated by Amidines
Wu, Yufeng,Zhou, Guangli,Meng, Qingwei,Tang, Xiaofei,Liu, Guangzhi,Yin, Hang,Zhao, Jingnan,Yang, Fan,Yu, Zongyi,Luo, Yi
, p. 13051 - 13062 (2018/10/25)
An aerobic photoepoxidation of α,β-unsaturated ketones driven by visible light in the presence of tetramethylguanidine (3b), tetraphenylporphine (H2TPP), and molecular oxygen under mild conditions was revealed. The corresponding α,β-epoxy ketones were obtained in yields of up to 94% in 96 h. The reaction time was shortened to 4.6 h by flow synthesis. The mechanism related to singlet oxygen was supported by experiments and density functional theory (DFT) calculations.
Chiral calcium-catalyzed asymmetric epoxidation reactions using hydrogen peroxide as the terminal oxidant
Yamashita, Yasuhiro,Macor, Joseph Alexander,Fushimi, Seiya,Tsubogo, Tetsu,Kobayashi, Shū
, p. 847 - 850 (2018/09/10)
Asymmetric epoxidation reactions of chalcone derivatives catalyzed by chiral calcium complexes using hydrogen peroxide were developed. The epoxidation reactions proceeded smoothly to afford the desired products in good yields with good enantioselectivitie
Visible-Light-Driven Epoxyacylation and Hydroacylation of Olefins Using Methylene Blue/Persulfate System in Water
De Souza, Gabriela F. P.,Bonacin, Juliano A.,Salles, Airton G.
, p. 8331 - 8340 (2018/07/21)
A visible-light-driven strategy for hydroacylation and epoxyacylation of olefins in water using methylene blue as photoredox catalyst and persulfate as oxidant is reported. In this unprecedented unified approach, two different transformations are accomplished using only one set of reagents. The method has a broad scope spanning a range of aromatic and aliphatic aldehydes as well as conjugated and nonconjugated olefins to deliver ketones and epoxyketones from abundant and inexpensive chemical feedstocks.
Facile epoxidation of α, β-unsaturated ketones with urea-2,2-dihydroperoxypropane as a new oxidant
Khosravi, Kaveh,Naserifar, Shirin
, p. 323 - 328 (2017/01/10)
Abstract: Various aromatic α, β-unsaturated ketones were successfully transformed into their corresponding epoxides using urea-2,2-dihydroperoxypropane as the oxygen source for the first time. The reactions were carried out under mild alkaline conditions at room temperature in high yields and short reaction times. Graphical Abstract: [Figure not available: see fulltext.]
Metal-Free and Efficient Epoxidation of α,β-Unsaturated Ketones with 1,1,2,2-Tetrahydroperoxy-1,2-Diphenylethane as a Powerful Solid Oxidant
Khosravi, Kaveh,Naserifar, Shirin,Mahmoudi, Boshra
, p. 683 - 689 (2017/06/19)
1,1,2,2-Tetrahydroperoxy-1,2-diphenylethane was used for the efficient and metal-free epoxidation of various α,β-unsaturated ketones, carried out under mild alkaline conditions at room temperature.
