141545-22-4Relevant academic research and scientific papers
Bisoxazolidine-catalyzed enantioselective reformatsky reaction
Wolf, Christian,Moskowitz, Max
, p. 6372 - 6376 (2011)
A readily available chiral bisoxazolidine catalyzes the asymmetric Reformatsky reaction between ethyl iodoacetate and aldehydes. In the presence of 10 mol % of the ligand, dimethylzinc, and air, this method produces ethyl 3-hydroxy-3-(4-aryl)propanoates in high yields and in 75 to 80% ee at room temperature within 1 h. In contrast to aromatic substrates, relatively low ee's are obtained with aliphatic aldehydes.
Catalytic enantioselective Reformatsky reaction with aldehydes
Fernandez-Ibanez, M. Angeles,Macia, Beatriz,Minnaard, Adriaan J.,Feringa, Ben L.
, p. 1317 - 1319 (2008)
(Chemical Presented) 120 years after the discovery of the Reformatsky reaction, the first effective catalytic enantioselective Reformatsky reaction with aldehydes using a binol derivative as a chiral catalyst is presented (see scheme; TMS = trimethylsilyl
Tridentate nitrogen phosphine ligand containing arylamine NH as well as preparation method and application thereof
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Paragraph 0103-0104; 0110-0114, (2021/06/26)
The invention discloses a tridentate nitrogen phosphine ligand containing arylamine NH as well as a preparation method and application thereof, and belongs to the technical field of organic synthesis. The tridentate nitrogen phosphine ligand disclosed by the invention is the first case of tridentate nitrogen phosphine ligand containing not only a quinoline amine structure but also chiral ferrocene at present, a noble metal complex of the type of ligand shows good selectivity and extremely high catalytic activity in an asymmetric hydrogenation reaction, meanwhile, a cheap metal complex of the ligand can also show good selectivity and catalytic activity in the asymmetric hydrogenation reaction, and is very easy to modify in the aspects of electronic effect and space structure, so that the ligand has huge potential application value. A catalyst formed by the ligand and a transition metal complex can be used for catalyzing various reactions, can be used for synthesizing various drugs, and has important industrial application value.
Method for preparing chiral beta-hydroxycarboxylate compound
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Paragraph 0061-0067, (2019/08/20)
The invention provides a method for preparing a chiral beta-hydroxycarboxylate compound, comprising the following steps: dissolving [Ir(COD)Cl]2, a ligand and an alkaline additive in a solvent, stirring at room temperature, carrying out in-situ synthesis of a catalyst, dissolving a substrate beta-hydroxycarboxylate compound in a solvent, adding the prepared catalyst, and introducing hydrogen to carry out an asymmetric catalytic hydrogenation reaction on the substrate beta-hydroxycarboxylate compound. The reaction conditions are as follows: pressure is 10-100 atmospheres, the reaction temperature is 0-200 DEG C, and the reaction time is 12-48 hours. The reaction activity and selectivity are high, and the hydrogenation reaction conditions are mild. The method is suitable for various beta-hydroxycarboxylate compounds; the substrate application range is wide; and the reaction process causes little environmental pollution.
Efficient P-Chiral Biaryl Bisphosphorus Ligands for Palladium-Catalyzed Asymmetric Hydrogenation
Jiang, Wenhao,Zhao, Qing,Tang, Wenjun
supporting information, p. 153 - 156 (2018/01/05)
A series of structurally novel P-chiral biaryl bisphosphorus ligands L1-L5 (BABIBOPs) are developed, providing high efficiency for the first time in palladium-catalyzed asymmetric hydrogenation of β-aryl and β-alkyl substituted β-keto esters. With the Pd-L3 (iPr-BABIBOP) catalyst, a series of chiral β-hydroxyl carboxylic esters are formed in excellent enantioselectivities (up to>99% ee) and yields at catalyst loading as low as 0.01 mol%.
Biaryl diphosphine ligand as well as preparation method and application thereof
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Paragraph 0265; 0266; 0267; 0268; 0269, (2018/05/16)
The invention discloses a biaryl diphosphine ligand as well as a preparation method and an application thereof. A biaryl diphosphine ligand compound represented as the formula I in the description ora biaryl diphosphine ligand enantiomer is provided, wherein R is alkyl of C1-C10 or naphthenic base of C3-C30 independently; Ra is hydrogen, alkyl of C1-C10, alkoxy of C1-C4, naphthenic base of C3-C30, halogen, R substituted or unsubstituted phenyl, R substituted or unsubstituted aryl of C10-C30 and R substituted or unsubstituted ceteroary of C4-C15 independently; all R, R and R are halogen, alkyl of C1-C4 or alkoxy of C1-C4 independently. With the adoption of the biaryl diphosphine ligand compound I, a series of chiral beta-hydroxy carboxylates with high optical purity can be effectively prepared through catalyzed synthesis, and the compound is high in economic practicability.
Microbiological bio-reduction of prochiral carbonyl compounds by antimycotic agent Boni Protect
Ko?odziejska, Renata,Studzińska, Renata,Kwit, Marcin,Jelecki, Maciej,Tafelska-Kaczmarek, Agnieszka
, p. 81 - 84 (2017/08/10)
The selective properties of the fungus Aureobasidium pullulans, in the antifungal agent Boni Protect, were investigated in the fermentative bioreduction of selected carbonyl compounds. Catalyzed by oxidoreductases contained in the microorganism Aureobasidium pullulans highly enantioselective biotransformation of prochiral ketones provides the secondary alcohols when the reaction is done in the presence of specific additives. Aureobasidium pullulans has also proved to be an effective bioreagent in the reduction of α- and β-keto esters. Optically pure hydroxy esters were obtained under fermentation conditions without the use of additives.
Asymmetric transfer hydrogenation of aryl ketoesters with a chiral double-chain surfactant-type catalyst in water
Li, Jiahong,Lin, Zechao,Huang, Qingfei,Wang, Qiwei,Tang, Lei,Zhu, Jin,Deng, Jingen
supporting information, p. 5367 - 5370 (2017/11/22)
A chiral double-chain surfactant-type ligand was designed and synthesized. The rhodium catalyst formed from the ligand can self-assemble into chiral vesicular aggregates in water, which was applied to the ATH of a broad range of aromatic ketoesters in neat water and gave up to 99% yield and 99% ee. In addition, this double-chain surfactant-type catalyst could also be applied to the dynamic kinetic resolution (DKR) of bicyclic β-ketoesters in water.
Asymmetric reformatsky reaction of aldehydes catalyzed by novel β -amino alcohols and zinc complexes
Li, Yan,He, Bin
supporting information, p. 1938 - 1943 (2014/07/07)
A series of β-amino alcohols derived from (1R, 2S)-2-amino-1,2- diphenylethanol and substituted salicylaldehydes as novel chiral tridentate ligands has been applied to an asymmetric Reformatsky reaction of aldehydes with ethyl iodoacetate in the presence
PH-independent transfer hydrogenation in water: Catalytic, enantioselective reduction of β-keto esters
Ariger, Martin A.,Carreira, Erick M.
supporting information, p. 4522 - 4524 (2012/10/29)
A pH-independent asymmetric transfer hydrogenation of β-keto esters in water with formic acid/sodium formate is described. The reaction is conducted open to air and gives access to β-hydroxy esters in excellent yields and selectivities.
