6781-44-8Relevant academic research and scientific papers
Preparation method 1,3 - diacyl benzene
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Paragraph 0046-0052; 0062-0075, (2021/08/25)
The preparation method of 1-3 - diacyl benzene comprises the following steps: reacting m-phthalic aldehyde with an alkyl magnesium halide to form an intermediate as shown II. The intermediate shown in Formula II is subjected to an oxidation reaction under the action of an oxidant to generate III, 1 diacyl benzene as shown 3 . In-flight R1 . R2 Alkyl groups from the alkyl magnesium halides, respectively. The method has the advantages of simple process, safety, environmental protection, high target product yield, high purity and the like, and can realize large-scale industrial production.
Multi-substituted chiral (1 - hydroxyethyl) benzene and asymmetric synthesis method thereof
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Paragraph 0047-0049; 0064-0066, (2021/07/01)
The invention relates to polysubstituted chiral (1-ethoxy)benzene. The specific structure of the polysubstituted chiral (1-ethoxy)benzene is as shown in a formula II. The invention also discloses a 'two-step one-pot' synthetic method of the polysubstituted chiral (1-ethoxy)benzene. The 'two-step one-pot' synthetic method is characterized by taking polyacetylenyl substituted benzene (I) as a raw material, and comprises the following steps: step (1) taking fluorine-containing alcohol and water as solvents, carrying out hydration reaction under the catalysis of trifluoromethanesulfonic acid, thusgenerating an intermediate-ketone; step (2) directly adding a complex of mono-sulfonyl chiral diamine and metal ruthenium, rhodium or iridium as a catalyst in a reaction system, adding alkali, supplementing hydrogen, and carrying out asymmetric hydrogenation reaction, thus obtaining a product II; or directly adding the complex of the mono-sulfonyl chiral diamine and the metal ruthenium, rhodium or iridium as the catalyst in the reaction system, using a mixture of sodium formate or formic acid and triethylamine as a hydrogen source, and carrying out the asymmetric transfer hydrogenation reaction, thus obtaining the product II. According to the 'two-step one-pot' synthetic method disclosed by the invention, the operation is simple, the raw material is easy to obtain, and enantioselectivityand diastereoselectivity are very high. (The formula II is shown in the description).
One-pot synthesis of chiral alcohols from alkynes by CF3SO3H/ruthenium tandem catalysis
Liu, Huan,Liu, Sensheng,Zhou, Haifeng,Liu, Qixing,Wang, Chunqin
, p. 14829 - 14832 (2018/04/30)
A practical one-pot synthesis of chiral alcohols from readily available alkynes via tandem catalysis by the combination of CF3SO3H and a fluorinated chiral diamine Ru(ii) complex in aqueous CF3CH2OH is described. Very interestingly, the combination of fluorinated catalysts and solvent exhibits a positive fluorine effect on the reactivity and enantioselectivity. A range of chiral alcohols with wide functional group tolerance was obtained in high yield and excellent stereoselectivity under simple and mild conditions.
Transformation of Alkynes into Chiral Alcohols via TfOH-Catalyzed Hydration and Ru-Catalyzed Tandem Asymmetric Hydrogenation
Liu, Sensheng,Liu, Huan,Zhou, Haifeng,Liu, Qixing,Lv, Jinliang
, p. 1110 - 1113 (2018/02/23)
A novel full atom-economic process for the transformation of alkynes into chiral alcohols by TfOH-catalyzed hydration coupled with Ru-catalyzed tandem asymmetric hydrogenation in TFE under simple conditions has been developed. A range of chiral alcohols was obtained with broad functional group tolerance, good yields, and excellent stereoselectivities.
Varying the ratio of formic acid to triethylamine impacts on asymmetric transfer hydrogenation of ketones
Zhou, Xiaowei,Wu, Xiaofeng,Yang, Bolun,Xiao, Jianliang
experimental part, p. 133 - 140 (2012/05/20)
Asymmetric transfer hydrogenation (ATH) is frequently carried out in the azeotropic mixture of formic acid (F) and triethylamine (T), where the F/T molar ratio is 2.5. This study shows that the F/T ratio affects both the reduction rate and enantioselectivity, with the optimum ratio being 0.2 in the ATH of ketones with the Ru-TsDPEN catalyst. Under such conditions, a range of substrates have been reduced, affording high yields and good to excellent enantioselectivities. In comparison with the common azeotropic F-T system, the reduction is faster. This protocol improves both the classic azeotropic and the aqueous-formate system when using water-insoluble ketones.
Sequential Birch reaction and asymmetric Ir-catalyzed hydrogenation as a route to chiral building blocks
Paptchikhine, Alexander,Itto, Kaori,Andersson, Pher G.
, p. 3989 - 3991 (2011/06/09)
A range of 1,2,4-trisubstituted cyclohexadienes obtained from the Birch reaction were hydrogenated asymmetrically to produce synthetically valuable chiral compounds in high enantio- and diastereoselectivity. The Royal Society of Chemistry.
Aminocyclopentadienyl Ruthenium Complexes as Racemization Catalysts for Dynamic Kinetic Resolution of Secondary Alcohols at Ambient Temperature
Choi, Jun Ho,Choi, Yoon Kyung,Kim, Yu Hwan,Park, Eun Sil,Kim, Eun Jung,Kim, Mahn-Joo,Park, Jaiwook
, p. 1972 - 1977 (2007/10/03)
Aminocyclopentadienyl ruthenium complexes, which can be used as room-temperature racemization catalysts with lipases in the dynamic kinetic resolution (DKR) of secondary alcohols, were synthesized from cyclopenta-2,4-dienimines, Ru3(CO)12, and CHCl 3: [2,3,4,5-Ph4(η5-C 4CNHR)]Ru-(CO)2Cl (4: R = i-Pr; 5: R = n-Pr; 6: R = t-Bu), [2,5-Me2-3,4-Ph2(η5-C 4CNHR)]Ru(CO)2Cl (7: R = i-Pr; 8: R = Ph), and [2,3,4,5-Ph4(η5-C4CNHAr)]Ru(CO) 2Cl (9: Ar =p-NO2C6H4; 10: Ar = p-ClC6H4; 11: Ar = Ph; 12: Ar = p-OMeC6H 4; 13: Ar = p-NMe2C6H4). The tests in the racemization of (S)-4-phenyl-2-butanol showed that 7 is the most active catalyst, although the difference decreased in the DKR. Complex 4 was used in the DKR of various alcohols; at room temperature, not only simple alcohols but also functionalized ones such as allylic alcohols, alkynyl alcohols, diols, hydroxyl esters, and chlorohydrins were successfully transformed to chiral acetates. In mechanistic studies for the catalytic racemization, ruthenium hydride 14 appeared to be a key species. It was the major organometallic species in the racemization of (S)-1-phenylethanol with 4 and potassium tert-butoxide. In a separate experiment, (S)-1-phenylethanol was racemized catalytically by 14 in the presence of acetophenone.
Highly enantioselective reduction of symmetrical diacetylaromatics with baker's yeast
Uchiyama, Masahiko,Katoh, Nobuo,Mimura, Rio,Yokota, Naoko,Shimogaichi, Yuki,Shimazaki, Makoto,Ohta, Akihiro
, p. 3467 - 3474 (2007/10/03)
Asymmetric reduction of symmetrical diacetylaromatics (1a, 1b, and 1d- g) with baker's yeast (Saccharomyces cerevisiae) provided the corresponding alcohols of high enantiomeric purity. By choosing appropriate reaction conditions, the products were preferentially the monoalcohols over the diols.
An efficient preparation of optically pure C2-symmetric aromatic diols by the asymmetric reduction of diacylaromatic compounds with B- chlorodiisopinocampheylborane
Ramachandran,Chen,Lu,Brown
, p. 3795 - 3798 (2007/10/03)
Asymmetric reduction of diacylaromatic compounds with B- chlorodiisopinocampheylborane provides the product diols in excellent diastereomeric and enantiomeric purity.
Separation of Remote Diol and Triol Stereoisomers by Enzyme-Catalyzed Esterification in Organic Media or Hydrolysis in Aqueous Media
Wallace, J. Shield,Baldwin, Bruce W.,Morrow, Cary J.
, p. 5231 - 5239 (2007/10/02)
The separation of symmetric, remote, secondary diol stereoisomers by stereoselective enzyme-catalyzed acetylation with acetic anhydride in anhydrous, low polarity organic solvents or by stereoselective enzyme-catalyzed hydrolysis of the corresponding pera
