33037-08-0Relevant 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.).
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.
One approach to cyclic carbonates via a three-component cyclization of phenacyl bromide, CO2, and aldehyde
Yan, Peng,Tan, Xueqin,Jing, Huanwang,Duan, Shuhui,Wang, Xiaoxuan,Liu, Zhongli
experimental part, p. 2459 - 2464 (2011/05/14)
A three-component cyclization reaction was designed for synthesizing cyclic carbonates in a single operation from phenacyl bromide, CO2, and aldehyde in the presence of lithium diisopropylamide (LDA). These novel reactions were achieved under extremely mild conditions to generate the target products in moderate to good yields within 10 min.
Intramolecular Friedel-Crafts alkylation of chalcone epoxides using indium(III) chloride as an efficient catalyst
Ahmed, Naseem,Babu, B. Venkata,Kumar, Harendra
experimental part, p. 2471 - 2477 (2011/09/19)
Indium(III) chloride catalyzes the ring opening of chalcone epoxides followed by intramolecular Friedel-Crafts alkylation under mild conditions at room temperature to afford highly functionalized 3-aryl-2-hydroxy-2,3-dihydro- 1H-inden-1-ones in excellent yields (81-95%). Georg Thieme Verlag Stuttgart, New York.
Facile epoxidation of α,β-unsaturated ketones with trans -3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane as an efficient oxidant
Azarifar, Davood,Khosravi, Kaveh
scheme or table, p. 2755 - 2758 (2010/12/25)
Application of trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane as an efficient oxygen source has been explored in the epoxidation of trans-chalcones. The reactions proceed under mild conditions at room temperature in alkaline solution to afford the corresponding epoxides in excellent yields.
Ring opening of α,β-epoxy phenyl ketones with eerie ammonium nitrate (CAN) and potassium bromide
Lu, Zhou,Wu, Wentao,Peng, Lijun,Wu, Longmin
, p. 142 - 145 (2008/09/18)
Ring-opening reaction of α,β-epoxy phenyl ketones was achieved cooperatively using cerium ammonium nitrate (CAN) and potassium bromide. The reaction occurred regioselectively at the β-C to afford syn-β-bromo-α-hydroxyl ketones as main outcomes.
Ionic liquid-grafted Mn(III)-Schiff base complex: A highly efficient and recyclable catalyst for the epoxidation of chalcones
Peng, Yanqing,Cai, Yueqin,Song, Gonghua,Chen, Jing
, p. 2147 - 2150 (2007/10/03)
A new Mn(III)-Schiff base complex with imidazolium phase tag was synthesized and employed as an efficient and recyclable catalyst for the epoxidation of chalcones with MCPBA/NMO. It can be recovered and reused (at least five times) without any loss of activity. Georg Thieme Verlag Stuttgart.
Michael-type addition of hydroxide to alkynylselenonium salt: Practical use as a ketoselenonium ylide precursor
Watanabe, Shin-Ichi,Asaka, Shinsuke,Kataoka, Tadashi
, p. 7459 - 7463 (2007/10/03)
A novel synthetic method of ketodiphenylselenonium ylide from alkynylselenonium salt is described. A reaction of alkynylselenonium salt, hydroxide ion, and aldehyde in the presence of silver triflate and triethylamine gave oxiranylketones just as a trans-
Kinetics of oxidation of styryl ketones by pyridinium chlorochromate
Mithula, M. Chandra,Murugesan, V.,Ananthakrishnanadar, P.
, p. 37 - 41 (2007/10/03)
The kinetics of oxidation of substituted styryl phenyl ketones and of substituted styryl methyl ketones by pyridinium chlorochromate (PCC) have been studied in 90percent acetic acid-10percent water (v/v) containing perchloric acid and NaClO4, at 30 deg, 40 deg, 50 deg and 60 deg C.The two reactions are first order each in ketones and PCC.The rate constants are well correlated with ?+ constants.The effects of varying and the percentage of acetic acid on the reaction rate have also been studied.A suitable mechanism has been proposed.
