146388-50-3Relevant articles and documents
A highly enantioselective synthesis of the odorant, 3-hydroxy-4- phenylbutan-2-one
Liang, Sen,Sun, Bao-Guo,Tian, Hong-Yu,Wang, Ya-Ling,Sun, Yu-Mei
, p. 105 - 106 (2013)
An efficient and highly enantioselective synthesis of 3-hydroxy-4- phenylbutan-2-one was developed involving the asymmetric epoxidation of an enone and hydrogenolysis of an α,β-epoxyketone. 1-Phenyl-3-buten-2-one was epoxidised with t-butyl hydroperoxide using a chiral La-BINOL-Ph3P=O complex as the catalyst to give (3S,4R)- or (3R,4S)- 3,4-epoxy-4-phenylbutan-2- one in ～90% yield and 97% ee. The resultant optically active epoxyketone was reduced in the presence of Pd/C (5 mol%) and H2 (3 bar) in THF at room temperature to produce (S)- or (R)-3-hydroxy-4-phenylbutan- 2-one in ～80% yield with more than 90% enantiomeric excess.
Water vs. desiccant. Improvement of Yb-BINOL complex catalyzed enantioselective epoxidation of enones
Watanabe, Shizue,Kobayashi, Yukari,Arai, Takayoshi,Sasai, Hiroaki,Bougauchi, Masahiro,Shibasaki, Masakatsu
, p. 7353 - 7356 (1998)
The Yb-BINOL-complex-catalyzed enantioselective epoxidation of α,β- unsaturated ketones (enones) was greatly improved by addition of a small amount of water (ca. 5 equiv to Yb). Optimized conditions and a plausible mechanism of the role of water and molec
Scoping the triphasic/PTC conditions for the Juliá-Colonna epoxidation reaction
Geller, Thomas,Krüger, Christa M.,Militzer, H.-Christian
, p. 5069 - 5071 (2004)
A new, highly efficient procedure for the Juliá-Colonna epoxidation is reported. Based on the original triphasic protocol it is shown that the co-catalysis of the reaction with phase transfer catalysts results in a dramatic increase of reactivity and some
Asymmetric epoxidation of enones employing polymeric α-amino acids in non-aqueous media
Bentley, Paul A.,Bergeron, Sophie,Cappi, Michael W.,Hibbs, David E.,Hursthouse, Michael B.,Nugent, Thomas C.,Pulido, Rosalino,Roberts, Stanley M.,Wu, L. Eduardo
, p. 739 - 740 (1997)
Urea-hydrogen peroxide complex in an organic solvent and in the presence of DBU and poly-(L)leucine causes rapid asymmetric epoxidation of the enones 1a, b and d.
Stereodivergent Access to Enantioenriched Epoxy Alcohols with Three Stereogenic Centers via Ruthenium-Catalyzed Transfer Hydrogenation
Zhao, Zhifei,Bagdi, Prasanta Ray,Yang, Shuang,Liu, Jinggong,Xu, Weici,Fang, Xinqiang
supporting information, p. 5491 - 5494 (2019/08/01)
The resolution technique of stereodivergent reaction on racemic mixtures (stereodivergent RRM) was employed for the first time in ruthenium complex catalyzed transfer hydrogenation of racemic epoxy ketones, providing a new and very simple method that allows access to enantioenriched epoxy alcohols with three stereogenic centers in a one-step fashion. The protocol features simple reaction conditions, practical operation, ability to scale up, and broad group tolerance.
Preparation method of alpha, beta-epoxy ketone compound
-
Paragraph 0036-0039, (2019/07/29)
The invention provides a method for efficiently preparing an alpha, beta-epoxy ketone compound from alpha-hydrogen-containing alpha-halogenated ketone as a raw material and various aldehydes under theaction of DBU or DBN. Namely the method comprises the steps: slowly and dropwise adding a dichloromethane mixed solution of alpha-halogenated ketone and aldehydes into a dichloromethane solution of DBU or DBN under the conditions of inert gas shielding and 20 DEG C below zero, ending a reaction, and then, carrying out separation and purification to obtain the alpha, beta-epoxy ketone compound. The synthesis method provided by the invention is available in raw material, low in cost, simple and easily-controlled in operation, relatively few in side reactions, simple in aftertreatment, relatively high in product yield, capable of greatly reducing the production cost, relatively high in economic benefit and suitable for large-scale industrial production.
Biomimetic Oxidative Deamination Catalysis via ortho-Naphthoquinone-Catalyzed Aerobic Oxidation Strategy
Golime, Gangadhararao,Bogonda, Ganganna,Kim, Hun Young,Oh, Kyungsoo
, p. 4986 - 4990 (2018/05/14)
An ortho-naphthoquinone-catalyzed oxidative deamination reaction has been developed where the molecular oxygen and water serve as the sole oxidant and nucleophile. The current aerobic deamination reaction proceeds via the ketimine formation between ortho-naphthoquinones and amines followed by the prototropic rearrangement and hydrolysis by water, representing a biomimetic oxidative deamination of amine species in the human body by the liver and kidneys. The compatibility of ortho-naphthoquinone organocatalysts with molecular oxygen and water opens up a new biomimetic catalyst system that can function as versatile deaminases for a variety of amine-containing molecules such as amino acids and DNA nuclear bases.
