1759-71-3Relevant academic research and scientific papers
Efficient preparation of vic-diacetates from epoxides and acetic anhydride in the presence of iron(III)-substituted polyoxometalate as catalyst
Yadollahi, Bahram,Esfahani, Farhad Kabiri
, p. 676 - 677 (2007)
Iron(III)-substituted polyoxometalate (TBA)4PFeW 11O39· 3H2O, has been demonstrated as an efficient catalyst in the ring opening of 1,2-epoxides with acetic anhydride for the one-pot synthesis of 1,2-diol esters in high to excellent yields under solvent-free condition. Copyright
Heterogeneous acidic and eco-friendly reagents for mild and convenient conversion of epoxides to 1,2-diacetates
Gilanizadeh, Masumeh,Zeynizadeh, Behzad
, p. 296 - 298 (2016)
A highly regioselective ring-opening of epoxides with acetic anhydride in the presence of hydrated disodium hydrogen phosphate and sodium hydrogen sulfate as efficient and eco-friendly reagents is described. The reactions are clean and lead to 1,2-diacetates in high to excellent yields.
Oxidation of Olefins with Benzenetelluric Anhydride
Kambe, Nobuaki,Tsukamoto, Takashi,Miyoshi, Noritaka,Murai, Shinji,Sonoda, Noboru
, p. 269 - 272 (1987)
Olefins were found to be oxidized by use of benzenetellurinic anhydride in acetic acid leading to vic-diacetates.Benzenetellurenic acid derivatives formed in situ are suggested as the active species.This diacetoxylation proceeds in net syn fashion probably via anti acetoxytellurenylation of the olefin followed by displacement of the phenyltelluro group by an acetoxy group with inversion.
Diol-Ritter Reaction: Regio- And Stereoselective Synthesis of Protected Vicinal Aminoalcohols and Mechanistic Aspects of Diol Monoester Disproportionation
Ondari, Mark E.,Klosin, Jerzy,Kruper, William R.,Lysenko, Ivan,Thomas, Pulikkottil J.,Cheng, Kevin,Abboud, Khalil A.,Kruper, William J.
, p. 2063 - 2074 (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.
Vicinal Difunctionalization of Alkenes under Iodine(III) Catalysis involving Lewis Base Adducts
Aertker, Kristina,Rama, Raquel J.,Opalach, Julita,Mu?iz, Kilian
supporting information, p. 1290 - 1294 (2017/04/18)
The influence of a 2-pyridinyl substituent on the catalytic performance of aryl iodides as catalyst in iodine(III) chemistry was explored. An efficient Lewis base adduct between the pyridine nitrogen and the electrophilic iodine(III) center was identified and confirmed by X-ray analysis. This arrangement was shown to generate a kinetically competent superior catalyst structure for the catalytic dioxygenation of alkenes. It introduces the concept of Lewis base adduct formation as a kinetic factor in iodine(I/III) catalysis. (Figure presented.).
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.
A trans -1,2-cyclohexanediol diacetate method for the preparation of
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Paragraph 0035-0043, (2017/05/30)
The invention discloses a preparation method of trans-1,2-cyclohexanol glycol diacetate. The preparation method comprises the following steps: (1) adding trans-1,2-cyclohexanol glycol and an esterification catalyst into a reaction container, then adding a reaction solvent, and heating to ensure that the trans-1,2-cyclohexanol glycol and the esterification catalyst are completely dissolved; (2) heating the reaction solution while stirring to boil the reaction solution, and when an organic phase overflow layered in a refluxing water separator returns to the reaction container, dropwise adding an esterifying agent into the reaction solution, and continuously reacting after dropwise adding the esterifying agent until the esterification reaction is finished; and (3) performing filtration, alkali cleaning, water washing and rectification on a reaction product to obtain the trans-1,2-cyclohexanol glycol diacetate. The preparation method disclosed by the invention is high in yield, low in investment and running costs and simple in production process, and is easy to realize industrial large-scale production.
Direct transformation of epoxides to 1,2-diacetates with Ac2O/B(OH)3 system
Gilanizadeh, Masumeh,Zeynizadeh, Behzad
, p. 1234 - 1238 (2016/01/12)
Direct transformation of different kinds of epoxides to 1,2-diacetates was carried out easily and efficiently with Ac2O/B(OH)3 system. All reactions were carried out under reflux conditions within 2 h to afford 1,2-diacetates in high yields.
A photoinduced cyclization cascade - Total synthesis of (-)-leuconoxine
Pfaffenbach, Magnus,Gaich, Tanja
supporting information, p. 6355 - 6357 (2015/04/22)
A protecting-group-free and enantioselective total synthesis of the monoterpenoid indole alkaloid (-)-leuconoxine was accomplished. The key step comprises a novel photoinduced domino macrocyclization/transannular cyclization involving the Witkop cyclization, for which additional mechanistic evidence is provided. This process furnishes a diaza[5.5.6.6]fenestrane skeleton, which is a hitherto unprecedented structure element.
Prilezhaev dihydroxylation of olefins in a continuous flow process
Van Den Broek, Bas A. M. W.,Becker, René,K?ssl, Florian,Delville, Mari?lle M. E.,Nieuwland, Pieter J.,Koch, Kaspar,Rutjes, Floris P. J. T.
experimental part, p. 289 - 292 (2012/06/01)
Epoxidation of both terminal and non-terminal olefins with peroxy acids is a well-established and powerful tool in a wide variety of chemical processes. In an additional step, the epoxide can be readily converted into the corresponding trans-diol. Batch-wise scale-up, however, is often troublesome because of the thermal instability and explosive character of the peroxy acids involved. This article describes the design and semi-automated optimization of a continuous flow process and subsequent scale-up to preparative production volumes in an intrinsically safe manner. Olefins go with the flow: Prilezhaev dihydroxylation can be performed on a large scale in continuous flow microreactor systems in the oxidation of terminal and internal olefins. Major drivers for a continuous flow process include better control, improved safety, and a faster overall process, leading to a significantly higher throughput. Copyright
