147220-19-7Relevant academic research and scientific papers
Kinetic study of addition of some carboxylic acids to 1,2-epoxy-3-phenoxypropane
Bukowska, Agnieszka,Bukowski, Wiktor
, p. 432 - 436 (1999)
The kinetics of addition of acetic, acrylic, or methacrylic acids to l,2-epoxy-3-phenoxypropane (glycidyl phenyl ether) carried out in the presence of chromium(III) ethanoate have been studied. A kinetic model of the reaction has been proposed. The rate constants as well as the activation parameters have been evaluated. The reactivity of the acids in reactions with GPE and 1-chloro-2,3-epoxypropane (epichlorohydrin) without any solvent are compared. The compositions of reaction mixtures have been carefully determined.
Diol-Ritter Reaction: Regio- And Stereoselective Synthesis of Protected Vicinal Aminoalcohols and Mechanistic Aspects of Diol Monoester Disproportionation
Abboud, Khalil A.,Cheng, Kevin,Klosin, Jerzy,Kruper, William J.,Kruper, William R.,Lysenko, Ivan,Ondari, Mark E.,Thomas, Pulikkottil J.
, (2021/10/20)
The well-known epoxide-Ritter reaction generally affords oxazolines with poor to average regioselectivity. Herein, a mechanism-based study of the less known diol-Ritter reaction has provided a highly regioselective procedure for the synthesis of 1-vic-amido-2-esters from either terminal epoxides or 1,2-diols via Lewis acid-catalyzed monoesterification. When treated with a stoichiometric Lewis acid catalyst (BF3), these diol monoesters form dioxonium cation intermediates that are ring-opened with nitrile nucleophiles to form nitrilium intermediates, which undergo rapid and irreversible hydration to give the desired amidoesters. Diester byproduct formation is irreversible and appears to occur through disproportionation of diol monoester. With chiral epoxide starting materials, the formation of amidoester occurs with retention of configuration and no apparent erosion of optical purity as determined by single-crystal X-ray analyses and chiral chromatography, respectively. The direct access to chiral vic-amidoesters is especially practical with regard to the synthesis of antibacterial oxazolidinone analogues of the Zyvox antimicrobial family.
Efficient and regioselective ring-opening of epoxides with carboxylic acid catalyzed by graphite oxide
Mirza-Aghayan, Maryam,Tavana, Mahdieh Molaee,Niazi, Elaheh Golam Alipour,Boukherroub, Rabah
, p. 532 - 538 (2020/07/17)
An efficient, simple and regioselective ring-opening reaction of epoxides with various carboxylic acids under metal-free conditions is reported. The ring-opening of epoxides takes place in the presence of graphite oxide as an efficient and available catalyst to produce the corresponding 2-hydroxy monoester and 1,2-diester derivatives in good yields. Regioselective attack of the nucleo-phile, short reaction times, metal-free conditions and reusability of catalyst are among the advantages of the present protocol.
Efficient resolution of 3-aryloxy-1,2-propanediols using CLEA-YCJ01 with high enantioselectivity
Wang, Bin,Wu, Bin,He, Bingfang
, p. 13757 - 13764 (2019/05/17)
The lipase YCJ01 from Burkholderia ambifaria is an organic solvent-stable enzyme and its activity can be activated by a hydrophobic solvent due to the "interface activation" mechanism. The activity of lipase YCJ01 increased by 2.1-fold with t-butanol as the precipitant even after cross-linking. The cross-linked enzyme aggregates of lipase YCJ01 (CLEAs-YCJ01) were found to be efficient for resolving 3-(4-methylphenoxy)-1,2-propanediol (MPPD) through sequential esterification. Excellent enantioselectivity towards MPPD (E > 400), excellent enantiomeric excess (ee) values of 99.2% for S-diacetates and 99.1% for R-monoacetate, and high yield (49.9%) were achieved using a high substrate concentration (180 mmol L-1). Thus, R- and S-type compounds with excellent ee values were simultaneously obtained, and MPPD was resolved by CLEAs-YCJ01. CLEAs-YCJ01 also showed high operational stability and maintained 91.2% residual activity after ten batches. To further evaluate the substrate specificity of CLEAs-YCJ01, a series of 3-aryloxy-1,2-propanediols (six analogues of MPPD) was applied as substrates for resolution. Under the optimized reaction conditions of reaction temperature of 35 °C, MPPD concentration of 180 mmol L-1, molar ratio of vinyl acetate to MPPD of 3 : 1, and isopropyl ether as the solvent, CLEAs-YCJ01 exhibited relatively strict enantioselectivity towards all the analogues of MPPD with a high yield (≥49.3%), favourable ee values (94.8-99.4%) for S-diacetates, and high ee values (92.1-99.2%) for R-monoacetate, which shows potential prospects for industrial applications.
A highly efficient protocol for regioselective ring-opening of epoxides with alcohols, water, acetic acid, and acetic anhydride catalyzed by SbF3
Zeynizadeh, Behzad,Gilanizadeh, Masumeh,Aminzadeh, Farkhondeh Mohammad
, p. 1051 - 1056 (2016/07/06)
SbF3as an efficient catalyst has been used for regioselective alcoholysis, acetolysis and hydrolysis of epoxides to the corresponding β-alkoxy, β-acetoxy alcohols, and 1,2-diols in high to excellent yields. This study also represents a convenient synthesis of vic-diacetates from ring-opening of epoxides with acetic anhydride.
Aniline-terephthalaldehyde resin p-toluenesulfonate (ATRT) as a highly efficient and reusable catalyst for alcoholysis, hydrolysis, and acetolysis of epoxides
Tanemura, Kiyoshi,Suzuki, Tsuneo
supporting information, p. 1781 - 1789 (2016/11/17)
Alcoholysis, hydrolysis, and acetolysis of epoxides were carried out in the presence of a catalytic amount of aniline-terephthalaldehyde resin p-toluenesulfonate (ATRT) to give the corresponding β-substituted alcohols in good yields. Alcoholysis and hydrolysis of epoxides catalyzed by ATRT proceeded faster than those by pyridinium p-toluenesulfonate (PPTS).
Synthesis and characterization of a novel Fe3O4@SiO2/bipyridinium dichloride nanocomposite and its application as a magnetic and recyclable phase-transfer catalyst in the preparation of β-azidoalcohols, β-cyanohydrins, and
Kiasat, Ali Reza,Chadorian, Fatemeh,Saghanezhad, Seyyed Jafar
, p. 1297 - 1306 (2015/12/11)
β-Azidoalcohols, β-cyanohydrins, and β-acetoxy alcohols have been synthesized in the presence of a Fe3O4@SiO2/bipyridinium nanocomposite (Fe3O4@SiO2/BNC) as a novel magnetic and recyclable
Regioselective acetylation of carbohydrates and diols catalyzed by tetramethyl-ammonium hydroxide in water
Lu, Yuchao,Wei, Peng,Pei, Yuxin,Xu, Hengfu,Xin, Xiaoting,Pei, Zhichao
, p. 4510 - 4514 (2014/12/10)
A novel method for an efficient regioselective acetylation of carbohydrates and diols in aqueous solution is described. Treatment of substrates with 1-acetylimidazole, and tetramethyl-ammonium hydroxide (TMAH) in water under mild conditions gave highly regioselective acetylation for primary hydroxyl groups. This discovery provides an eco-friendly way for selective acetylation of non-protected glycosides and diols in water, avoiding the use of toxic organic solvents and the necessity of pre-protection of secondary hydroxyl groups. This journal is
A biocatalytic approach for regioselective monoacetylation of 3-aryloxy-1,2-propanediols by porcine pancreatic lipase
Meena, Vachan Singh,Banerjee
experimental part, p. 951 - 953 (2012/08/29)
Among the various lipases screened for the regioselective monoacetylation of 3-aryloxy-1,2-propanediols, porcine pancreatic lipase was found to afford a higher yield. The selectivity for the monoacetylation process was maximized by using different organic solvents and diisopropyl ether gave the highest conversion to monoacetylated product (ca. 98%). The optimized reaction afforded excellent yields of the monoacetylated product with regioselectivity at the terminal hydroxyl group in the presence of various aryl substituents in the starting material. Springer-Verlag 2011.
Investigation of the catalytic activity of an electron-deficient vanadium(IV) tetraphenylporphyrin: A new, highly efficient and reusable catalyst for ring-opening of epoxides
Taghavi, S. Abdolmanaf,Moghadam, Majid,Mohammadpoor-Baltork, Iraj,Tangestaninejad, Shahram,Mirkhani, Valiollah,Khosropour, Ahmad Reza,Ahmadi, Venus
experimental part, p. 2244 - 2252 (2011/10/03)
In this work, the catalytic activity of high-valent tetraphenylporphyrinatovanadium(IV) trifluoromethanesulfonate, [V IV(TPP)(OTf)2], in the nucleophilic ring-opening of epoxides is reported. This new V(IV) catalyst was used as an efficient catalyst for alcoholysis with primary (methanol, ethanol and n-propanol), secondary (iso-propanol) and tertiary alcohols (tert-butanol), hydrolysis and acetolysis of epoxides with acetic acid and also for the conversion of epoxides to 1,2-diacetates with acetic anhydride, conversion of epoxides to thiiranes with ammonium thiocyanate and thiourea, and for conversion of epoxides to acetonides with acetone. The catalyst was reused several times without loss of its activity.
