90646-63-2Relevant 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.).
Efficient generation of hydrogen peroxide by aerobic photooxidation of 2-propanol using anthraquinone-2-carboxylic acid and one-pot epoxidation of α,β-unsaturated ketones
Cui, Lei,Furuhashi, Sohei,Tachikawa, Yuma,Tada, Norihiro,Miura, Tsuyoshi,Itoh, Akichika
, p. 162 - 165 (2013/02/21)
We developed an efficient method for the generation of hydrogen peroxide by aerobic photooxidation of 2-propanol using anthraquinone-2-carboxylic acid and molecular oxygen in air and visible light from fluorescent lamps. One-pot epoxidation of α,β-unsaturated ketones using the generated hydrogen peroxide is also reported.
Facial selectivity and stereospecificity in the (4 + 3) cycloaddition of epoxy enol silanes
Lo, Brian,Chiu, Pauline
supporting information; experimental part, p. 864 - 867 (2011/05/06)
The scope of the (4 + 3) cycloaddition using epoxy enol silanes has been examined. Unhindered and nucleophilic dienes react to give the highest yields, but hindered dienes give rise to higher diastereoselectivities. Notably, the cycloaddition shows facial
Amino-acid-mediated epoxidation of α,β-unsaturated ketones by hydrogen peroxide in aqueous media
Kim, Juhyun,Jung, Suhyun,Park, Seongsoon,Park, Sojung
experimental part, p. 2866 - 2868 (2011/06/21)
Amino acids, such as arginine and lysine, can be used as an efficient catalyst in the epoxidation of α,β-unsaturated ketones with aqueous hydrogen peroxide. Up to >99% conversion was obtained in the reaction toward 11 α,β-unsaturated ketones.
Catalytic enantioselective peroxidation of α,β-unsaturated ketones
Lu, Xiaojie,Liu, Yan,Sun, Bingfeng,Cindric, Brittany,Deng, Li
supporting information; body text, p. 8134 - 8135 (2009/02/02)
Despite the potential of chiral peroxides as biologically interesting or even clinically important compounds, no catalytic enantioselective peroxidation has been reported. With a chiral catalyst not only to induce enantioselectivity but also to convert a well established epoxidation pathway into a peroxidation pathway, the first efficient catalytic peroxidation has been successfully developed. Employing readily available α,β-unsaturated ketones and hydroperoxides and an easily accessible cinchona alkaloid catalyst, this novel reaction will open new possibilities in the asymmetric synthesis of chiral peroxides. Under different conditions a highly enantioselective epoxidation with the same starting materials, reagents, and catalyst has was also established. Copyright
Recyclable Polyurea-Microencapsulated Pd(0) Nanoparticles: An Efficient Catalyst for Hydrogenolysis of Epoxides
Ley, Steven V.,Mitchell, Claire,Pears, David,Ramarao, Chandrashekar,Yu, Jin-Quan,Zhou, Wuzong
, p. 4665 - 4668 (2007/10/03)
(Matrix presented) Pd nanoparticles (～2 nm in size) microencapsulated in polyurea is an efficient and recyclable catalyst for reductive ring-opening hydrogenolysis of epoxides, using either HCOOH/Et3N or H2 as a hydrogen donor.
Highly efficient epoxidation of α,β-unsaturated ketones by hydrogen peroxide with a base hydrotalcite catalyst prepared from metal oxides
Honma, Takayuki,Nakajo, Michiko,Mizugaki, Tomoo,Ebitani, Kohki,Kaneda, Kiyotomi
, p. 6229 - 6232 (2007/10/03)
The base hydrotalcite, prepared from MgO and Al2O3, acted as a highly efficient catalyst for the epoxidation of α,β-unsaturated ketones using aqueous hydrogen peroxide as an oxidant. This heterogeneous epoxidation has the advantages of a high efficiency of H2O2 utilization without organic solvents, a simple workup procedure, and reusability of the hydrotalcite catalyst.
Epoxidation of α,β-Unsaturated Ketones Using Hydrogen Peroxide in the Presence of Basic Hydrotalcite Catalysts
Yamaguchi, Kazuya,Mori, Kohsuke,Mizugaki, Tomoo,Ebitani, Kohki,Kaneda, Kiyotomi
, p. 6897 - 6903 (2007/10/03)
The basic layered hydrotalcites have been used as catalysts for the epoxidation of α,β-unsaturated ketones in heterogeneous reaction media using hydrogen peroxide as an oxidant. A wide variety of α,β-unsaturated ketones were oxidized to the corresponding epoxyketones in excellent yields under mild reaction conditions. For example, 2-cyclohexen-1-one gave 2,3-epoxycyclohexanone in 91% yield at 40°C for 5 h with high efficiency in hydrogen peroxide. The catalytic activity of the hydrotalcites increased as the basicity of their surfaces increased. In the case of the epoxidation of less reactive substrates, adding a cationic surfactant such as n-dodecyltrimethylammonium bromide (DTMAB) to the above oxidation system accelerated the epoxidation reaction. These hydrotalcite catalysts were easily separated from the reaction mixture and were reusable.
