Relevant bibliographies by topics / Acyloins

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  2. Dissertations / Theses
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  4. Book chapters

Academic literature on the topic 'Acyloins'

Author: Grafiati
Published: 4 June 2021
Last updated: 3 February 2022

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Journal articles on the topic "Acyloins"

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Patrzałek, Michał, Aleksandra Zasada, Anna Kajetanowicz, and Karol Grela. "Tandem Olefin Metathesis/α-Ketohydroxylation Revisited." Catalysts 11, no. 6 (June 9, 2021): 719. http://dx.doi.org/10.3390/catal11060719.

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EWG-activated and polar quaternary ammonium salt-tagged ruthenium metathesis catalysts have been applied in a two-step one-pot metathesis-oxidation process leading to functionalized α-hydroxyketones (acyloins). In this assisted tandem process, the metathesis catalyst is used first to promote ring-closing metathesis (RCM) and cross-metathesis (CM) steps, then upon the action of Oxone™ converts into an oxidation catalyst able to transform the newly formed olefinic product into acyloin under mild conditions.
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Gill, M., MJ Kiefel, DA Lally, and A. Ten. "Pigments of Fungi. XV. An Efficient, Unambiguous Route to Unsymmetrically Substituted Dibenzyl Acyloins and Their Use in the Synthesis of Fungus Pigments of the Pulvinone and Grevillin Types." Australian Journal of Chemistry 43, no. 9 (1990): 1497. http://dx.doi.org/10.1071/ch9901497.

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Dibenzyl acyloins including those bearing unsymmetrically disposed aryl residues are assembled in high yield by reaction between the O-trimethylsilyl ethers of arylacetaldehyde cyanohydrins and benzyl Grignard reagents. These acyloins are deprotonated with lithium diisopropylamide to afford alcoholate-enolate dianions which can be made to react with carbonyldiimidazole and with oxalyldiimidazole, respectively, to ultimately afford fungus pigments of the pulvinone and grevillin types.
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Neuser, Frauke, Holger Zorn, and Ralf G. Berger. "Formation of Aliphatic and Aromatic α-Hydroxy Ketones by Zygosaccharomyces bisporus." Zeitschrift für Naturforschung C 55, no. 7-8 (August 1, 2000): 560–68. http://dx.doi.org/10.1515/znc-2000-7-814.

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Abstract The wild-type yeast strain Zygosaccharomyces bisporus CBS 702 produced α-hydroxyketones (acyloins) from amino acid precursors after transamination to the corresponding 2-oxo acids. The key enzyme of the subsequent decarboxylation and C − C bond forming reaction, pyruvate decarboxylase (PDC ), was examined for its substrate- and stereo-specificity. A wide variety of saturated and unsaturated aliphatic and aromatic aldehydes was successfully converted to acyloins. 19 of the biotransformation products identified had not been reported as natural substances before. Product yields were strongly affected by substrate structure.
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Marples, Brian A., and Christopher D. Spilling. "Ene reactions of unsaturated acyloins." Tetrahedron Letters 26, no. 52 (January 1985): 6515–18. http://dx.doi.org/10.1016/s0040-4039(00)99041-5.

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Montgomery, J. A., M. Jetté, S. Huot, and C. Des Rosiers. "Acyloin production from aldehydes in the perfused rat heart: the potential role of pyruvate dehydrogenase." Biochemical Journal 294, no. 3 (September 15, 1993): 727–33. http://dx.doi.org/10.1042/bj2940727.

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Aldehydes represent an important class of cytotoxic products derived from free radical-induced lipid peroxidation which may contribute to reperfusion injury following myocardial infarct. Metabolism of aldehydes in the heart has not been well characterized aside from conjugation of unsaturated aldehydes with glutathione. However, aliphatic aldehydes like hexanal do not form stable glutathione conjugates. We have recently demonstrated in vitro that pig heart pyruvate dehydrogenase catalyses a reaction between pyruvate and saturated aldehydes to produce acyloins (3-hydroxyalkan-2-ones). In the present study, rat hearts were perfused with various aldehydes and pyruvate. Acyloins were generated from saturated aldehydes (butanal, hexanal or nonanal), but not from 2-hexanal (an unsaturated aldehyde) or malondialdehyde. Hearts perfused with 2 mM pyruvate and 10-100 microM hexanal rapidly took up hexanal in a dose-related manner (140-850 nmol/min), and released 3-hydroxyoctan-2-one (0.7-30 nmol/min), 2,3-octanediol (0-12 nmol/min) and hexanol (10-200 nmol/min). Small quantities of hexanoic acid (about 10 nmol/min) were also released. The rate of release of acyloin metabolites rose with increased concentration of hexanal, whereas hexanol release attained a plateau when hexanal infusion concentrations rose above 50 microM. Up to 50% of hexanal uptake could be accounted for by metabolite release. Less than 0.5% of hexanal uptake was found to be bound to acid-precipitable macromolecules. When hearts perfused with 50 microM hexanal and 2 mM pyruvate were subjected to a 15 min ischaemic period, the rates of release of 2,3-octanediol, 3-hydroxyoctan-2-one, hexanol and hexanoate during the reperfusion period were not significantly different from those in the pre-ischaemic period. Our results indicate that saturated aldehydes can be metabolically converted by the heart into stable diffusible compounds.
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Suárez, Anisley, Fernando Martínez, and Roberto Sanz. "Synthesis of α-functionalized α-indol-3-yl carbonyls through direct SN reactions of indol-3-yl α-acyloins." Organic & Biomolecular Chemistry 14, no. 47 (2016): 11212–19. http://dx.doi.org/10.1039/c6ob02125e.

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Liang, Deqiang, Xiangguang Li, Yanni Li, Yungang Yang, Shulin Gao, and Ping Cheng. "Br2-Catalyzed regioselective dehydrative coupling of indoles with acyloins: direct synthesis of α-(3-indolyl) ketones." RSC Advances 6, no. 35 (2016): 29020–25. http://dx.doi.org/10.1039/c6ra03321k.

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Firouzabadi, Habib, Babak Karimi, and Mohammad Abbassi. "Efficient Solvent-free Oxidation of Benzylic and Aromatic Allylic Alcohols and Biaryl Acyloins by Manganese Dioxide and Barium Manganate." Journal of Chemical Research 23, no. 3 (March 1999): 236–37. http://dx.doi.org/10.1177/174751989902300333.

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Ödman, Peter, Ludger A. Wessjohann, and Uwe T. Bornscheuer. "Chemoenzymatic Dynamic Kinetic Resolution of Acyloins." Journal of Organic Chemistry 70, no. 23 (November 2005): 9551–55. http://dx.doi.org/10.1021/jo051661n.

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Ostrowski, Karoline A., Thiemo A. Faßbach, and Andreas J. Vorholt. "Tandem Hydroformylation/Acyloin Reaction - The Synergy of Metal Catalysis and Organocatalysis Yielding Acyloins Directly from Olefins." Advanced Synthesis & Catalysis 357, no. 7 (April 23, 2015): 1374–80. http://dx.doi.org/10.1002/adsc.201401031.

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Dissertations / Theses on the topic "Acyloins"

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Simsek, Ilke. "Benzaldehyde Lyase Catalyzed Synthesis Of Novel Acyloins." Master's thesis, METU, 2009. http://etd.lib.metu.edu.tr/upload/12610901/index.pdf.

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-Hydroxy phosphonates are versatile building blocks for the synthesis of many biologically active compounds that display antiviral, antibacterial, anticancer, pesticide activities beside their enzyme inhibitory activities such as they are the inhibitors of rennin or human immunodeficiency virus (HIV) protease and polymerase. Benzaldehyde lyase is able to catalyze not only C-C bond formation reactions but also C-C bond breaking reactions with high enantioselectivity that brings about the development of new synthetic methodologies for the synthesis of hydroxy ketones which are the key intermediates in the synthesis of many biologically active compounds due to the versatility of stereogenic center for developing structural diversity. There are several synthetic methodologies for the synthesis of hydroxy phoshonates however, in this work we have achieved the synthesis of hydroxy phoshonates through C-C bond forming reactions catalyzed by Benzaldehyde lyase that offers the use of green methodologies. Moreover, we have achieved the synthesis of hydroxy ketones which are versatile building blocks in the synthesis of many biologically active compounds via the immobilization of BAL enzyme on superparamagnetic solid support with high yield and high enantioselectivity.
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Spilling, Christopher D. "The intramolecular ene reactions of some unsaturated acyloins." Thesis, Loughborough University, 1986. https://dspace.lboro.ac.uk/2134/25592.

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The reaction of 3β-tosyloxy-5α-cholesta-5,6β-diol with potassium t butoxide in t-butanol has been further investigated. 5β-Hydroxy-4,5-secocholest-3-en-6-one was synthesised. It was shown to undergo an ene reaction in decalin in a sealed tube at 200°C to give primarily 3β-methyl-A-nor-5β-cholestan-5-o1 -6-one and 6β-hydroxy-4(5-6α) abeo-cholestan-5-one. These primary products were further modified under the reaction conditions to give 3-methyl-B-nor-5β-cholest-2-en-4-one and 5β-cholestan-5-ol-6-one respectively. The cyclohexane analogue, 3-methyl-3-(3-butenyl)-2-hydroxy-cyclohexanl- one was synthesised. Heating under reflux in decalin gave 3β,7αβ-dimethyl- 3αβ-hydroxy-octahydro-4H-inden-4-one; 5β,7αβ-dimethyl-3αβ-hydroxy-octahydro- 4H-inden-4-one and an unidentified minor product. The synthesis of 5-(2-propenyl)-5β-cholestan-2-ol-3-one was partially completed. The epimeric 5-(2-propenyl)-5β-cholestan-2-ol-3-one was synthesised. The ene reaction was observed in refluxing toluene giving 2α,5-(1-methylethano)-5α-cholestan-2β-ol-3-one and 3α,5-(methyethano)-5α-cholestan-3βol-2-one. The ketone analogue, 5-(2-propenyl )-5α-cholestan-3-one underwent an ene reaction in decalin in a sealed tube at 250°C to give 2α,5-(1-methylethano) -5α-cholestan-3-one.
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Richter, Ulla. "Aminosäuren und aromatische Acyloine bei Wildhefen und Saccharomyces cerevisiae." [S.l. : s.n.], 1998. http://deposit.ddb.de/cgi-bin/dokserv?idn=954307038.

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Jahanshahi, Esfahani Ali. "Synthesis of oxygen containing functionalities : use of the acyloin and metathesis reaction in organic chemistry." Thesis, University of Oxford, 2012. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.559765.

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1. In the first part of this thesis, the concept of a tether based intramolecular crossed -acyloin reaction mediated by heterogeneous lithium/ 4,4' -di-teti-butylbiphenyl (Li/DBB) reducing conditions was examined. The objective of the project was to accomplish an intramolecular crossed-acyloin reaction, by employing non-symmetric di-esters, linked with a suitable tether (diol) between the two acyl functionalities. Chapter 1: Introduction - Acyloin Condensation. The concept of carbon-carbon coupling reactions between two carbonyl functionalities to synthesise a-hydroxyketone (acyloin) moieties is described. Generally, there are two methods, either by bimolecular reductive coupli ng of esters, known as acyloin condensation or the umpo/ung dimerisation of aldehydes, known as benzoin condensation. The background and recent developments in these reaction categori es are discussed in this section. In addition, this section outlines the project's aims and describes the previous work conducted in the group. Chapter 2: Results & Discussion - An Alternative Route to Crossed-ocyloin In this section, the tether based intramolecular crossed-acyloin reaction mediated by Li/DBB reducing conditions is introduced. This work is based on the hypothesis that a suitable tether, could promote an intramolecular crossed-acyloin reaction. The objective was successfully achieved through a series of competition experiments, which demonstrated that the application of exo-exo norbornenediol as a tether exclusively formed crossed-acyloin products. This discovery was accompanied by an investigation into regi oselective crossed-acyloin reaction. 2. In the second part of this thesis, the Sharpless Asymmetric Epoxidation (SAE) desymmetrisation reaction of O'-symmetric diene 1,3-diols was exami ned. It was suggested that formation of the epoxide would trigger a stereoselective 5-exo-tet ring closure to deliver predominately trans-THF adducts. Chapter 3: Introduction - Metal Mediated Synthetic Routes to trans-2,5-Disubstituted THFs This section introduces the transition metal mediated cyciisation of bishomoallylic alcohol, to the corresponding trans- THF moieties. In particular, the development and application of three methods were highlighted; rhenium mediated (3+2) oxidative cyclisation, cobalt catalysed oxidative cyclisation and an rc-allylpalladium complex catalysed reaction. In addition, the concept of the Sharpless Asymmetric Epoxidation (SAE) is introduced and the project objectives are outlined. Chapter 4: Results & Discussion - A NOJel Route Towards trans- THFs The primary effort was to design a robust route to form the test substrate, (3R,55}hepta-1,6-diene- 3,5-diol, which was accomplished in good yield by Ring Opening/Crossed metathesis (ROM) of silyl ether protected (1 R, 35 }cyclopent-4-ene-1,3-diol. The expe rimental results have demonstrated that SAE of the diene 1,3 diol formed trans-THF. Chapter 5: Experimental Full experimental procedures and characterisation of the synthesised molecules are reported.
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Rössle, Michael. "Cer-katalysierte Oxidationsreaktionen von [beta]-Dicarbonylverbindungen [Beta-Dicarbonylverbindungen]." Berlin mbv, 2008. http://d-nb.info/991428382/04.

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Sopaci, Saziye Betul. "Microorganism Mediated Stereoselective Bio-oxidation And Bio-hydrogenation Reactions And Thiamine Pyrophosphate Dependent Enzyme Catalyzed Enantioselective Acyloin Reactions." Phd thesis, METU, 2009. http://etd.lib.metu.edu.tr/upload/2/12610516/index.pdf.

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In this study various microbial and enzymatic methods developed for enantioselective acyloin synthesis for preparation of some pharmaceutically important intermediates. By performing Aspergillus flavus (MAM 200120) mediated biotransformation, enantioselective bio-oxidation of meso-hydrobenzoin was achieved with a high ee value (76%). Racemic form of hydrobenzoin was also employed for the same bio-oxidation process and this bioconversion was resulted in accumulation of meso form (>
90% yield) confirming the suggested mechanism of oxidation-reduction sequence of hydrobenzoin. Wieland-Miescher ketone (3,4,8,8a-tetrahydro-8a-methylnaphthalene-1,6(2H,7H)-dione) is an important starting material for bioactive compounds like steroids and terpenoids. Many synthetic approaches include enantioselective reduction of this compound. In this study Aspergillus niger (MAM 200909) mediated reduction of Wieland-Miescher ketone was achieved with a high yield (80%), de (79%) and ee (94%) value and these results were found much more superior than previously reported studies. Carboligating enzymes benzaldehyde lyase (BAL) (EC 4.1.2.38) and benzoiyl formate decarboxilase (BFD) (E.C. 4.1.1.7) are used for biocatalytic acyloin synthesis. These enzymes are immobilized to surface modified superparamagnetic silica coated nanoparticles by using metal ion affinity technique. With this system recombinant histidine tagged BAL and BFD purified and immobilized to magnetic particles by one-pot purification-immobilization procedure. SDS page analysis showed that our surface modified magnetic particles were eligible for specific binding of histidine tagged proteins. Conventional BAL and BFD catalyzed benzoin condenzation reactions and some representative acyloin reactions were performed with this system with a high enantioselectivity (99-92%) and yield. Results obtained with magnetic particle-enzyme system were also found comparable with that of free enzyme catalyzed reactions.
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Bornemann, Stephen. "Studies on pyruvate decarboxylase-catalysed acyloin formation and the effects of surfactants on lipase-catalysed hydrolysis of esters." Thesis, University of Warwick, 1992. http://wrap.warwick.ac.uk/110304/.

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The effect of surfactants on the hydrolysis of achiral and chiral substrates by crude and purified porcine pancreatic lipase (PPL; EC 3.1.1.3) has been studied. Rather than accelerating the reactions, surfactants slowed down ("inhibited") the reactions relative to the rate in the absence of surfactant, despite effective emulsification of the substrate. Surfactants varied in the extent to which the reaction was inhibited and inhibition occurred below the critical micelle concentration of surfactants. Inhibition was accompanied by a loss of enantioselectivity with the crude enzyme but not the purified enzyme, indicating the presence of more than one activity in the crude PPL preparation. In general, there would seem to be no advantage to be gained from the use of surfactants in the hydrolysis of compounds of low water solubility with lipolytic enzymes; the use of an immiscible cosolvent is more effective. The pyruvate decarboxylase (EC 4.1.1.1) from Zymomonas mobilis strain CP4 ATCC 31821 was purified from recombinant Escherichia coli harbouring the plasmid pLOI295, which contained the gene coding for the enzyme. The purified recombinant enzyme catalysed acyloin condensations with a number of aldehyde acceptors. The substrate specificity of the Zymomonas enzyme was very similar to that observed with the enzyme from Saccharomyces carlsbergensis. However, the Zymomonas enzyme was found to catalyse the formation of acyloins from acetaldehyde at a rate four orders of magnitute greater than that observed with yeast enzyme. By comparing the stereochemistry of acyloin condensations catalysed by the Zymomonas and yeast enzymes, differences in the architecture of the active sites of these closely related enzymes have emerged.
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Karkour, Belkacem. "Les cyclopropanols chiraux et leur potentialité synthétique." Paris 11, 1987. http://www.theses.fr/1987PA112378.

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Cette thèse décrit une voie d'accès aux cyclopropanols chiraux et en étudie les potentialités synthétiques. Préparé à partir du méthyl-2 succinate de n-butyle, l'hydroxy-1 méthyl-2 cyclopropanecarboxaldéhyde est un précurseur de (vinylcarbinol)-1 cyclopropanols lesquels, subissent en milieu acide soit une extension de cycle C3→C4 régiospécifique en vinyl-2 cyclobutanones (BF3-Et20), soit une extension de cycle C3→C4→C5 en cyclopentène-2 ones (CH3S03H-P205). La réaction thermique des méthyl-2 vinylcyclopropanes donne par ène-réaction des produits d'ouverture de cycle limitant l'intérêt du réarrangement vinylcyclopropane-cyclopentène ; ce problème est contourné par cette nouvelle approche. Les (R)(+) et (S)(-) méthyl-2 succinates de méthyle, préparés par résolution enzymatique à l'aide de la lipase du pancréas de porc, sont cyclisés par réaction du type acyloïne en (R) et (S) méthyl-3 disiloxycyclobutènes respectivement. Ceux-ci par régression de cycle stéréosélective C4 → C3 en milieu basique, donnent accès sans altération du centre chiral à des hydroxy-1 cyclopropanecarbo­ xaldéhydes, utilisés pour préparer des (vinylcarbinol)-1 cyclopropanols optiquement actifs. Une extension de cycle C3→C4 régio- et stéréospécifique conduit alors aux vinyl-2 cyclobutanones avec une très bonne énantiosélectivité. Ces composés ont été utilisés pour préparer la (S)(+) méthyl-5 cyclohexène-2-one et un buténolide : la quercus lactone b. Les vinyl-2 cyclobutanones sont des précurseurs de cycle en C5, C6 et C8, cette méthodologie, ne mettant pas en jeu d'ions cyclopropylcarbinyl vrais comme le prouve la stéréospécificité des réarrangements, permet donc, à partir de succinates chiraux, d'envisager la synthèse totale de produits naturels de structures variées
The aim of this thesis is the preparation and study of the synthetic potential of chiral cyclopropanols. The 1-hydroxy 2-methyl cyclopropanecarboxaldehyde available from 2-methylsuccinate, is used to prepare 1-(vinylcarbinol} cyclopropanols which, undergo acid induced C3 C4 regiospecific ring expansion into 2-vinyl cyclobutanones (BF3-Et20) or C3 -+ C4 --+- C5 ring expansion into cyclopenten-2- ones (CH3S03H-P205). The thermal rearrangement of 2-methyl vinylcyclopropanes leads by an ene-reaction to ring-opened products ; therefore the limitation of the thermal vinylcyclopropane-cyclopentene ring enlargement is removed by this new approach. (R)(+) and (S)(-). Dimethyl 2-methylsuccinates, now available from enantiose­ lective hydrolysis by porcine pancreatic lipase, undergo acyloin type cyclization into (R) and (S) 3-methyl-1,2-disiloxycyclobutene, respectively. Base-induced stereoselective C4 C3 ring contraction of these cyclobutenes provides 1-hydroxycyclopropanecarboxaldehydes which are used to prepare optically active 1-alkenylcyclopropanols. Then, acid-induced regio- and stereospecific C3---+ C4 ring enlargement leads to 2-vinylcyclobutanones with high enantiomeric excesses. These compounds are used to synthetize (S) 5-methyl cyclohexen-2-one and abutenolide ; i. E. The quercus lactone b2-Vinylcyclobutanones are efficient precursors of 5-, 6- and 8-membered rings. Therefore, this new methodology, which does not involve cyclopropylcarbiny1 cations as proven by the stereospecificity of the rearrangements, allows one to prepare from chiral succinates natural compounds bearing different frameworks
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Richter, Ulla [Verfasser]. "Aminosäuren und aromatische Acyloine bei Wildhefen und Saccharomyces cerevisiae / von Ulla Richter." 1998. http://d-nb.info/954307038/34.

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Books on the topic "Acyloins"

1

Bornemann, Stephen. Studies on pyruvate decarboxylase-catalysed acyloin formation and the effects of surfactants on lipase-catalysedhydrolysis of esters. [s.l.]: typescript, 1992.

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Spilling, C. D. The intramolecular ene reactions of some unsaturated acyloins. 1986.

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Book chapters on the topic "Acyloins"

1

Laue, Thomas, and Andreas Plagens. "Acyloin-Kondensation." In Teubner Studienbücher Chemie, 3–5. Wiesbaden: Vieweg+Teubner Verlag, 1994. http://dx.doi.org/10.1007/978-3-322-94726-0_2.

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Laue, Thomas, and Andreas Plagens. "Acyloin-Kondensation." In Teubner Studienbücher Chemie, 3–5. Wiesbaden: Vieweg+Teubner Verlag, 1998. http://dx.doi.org/10.1007/978-3-322-94077-3_2.

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Laue, Thomas, and Andreas Plagens. "Acyloin-Kondensation." In Teubner Studienbücher Chemie, 3–5. Wiesbaden: Vieweg+Teubner Verlag, 1994. http://dx.doi.org/10.1007/978-3-322-94015-5_2.

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Pohl, Martina, Carola Dresen, Maryam Beigi, and Michael Müller. "Acyloin and Benzoin Condensations." In Enzyme Catalysis in Organic Synthesis, 919–45. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2012. http://dx.doi.org/10.1002/9783527639861.ch22.

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Ward, Owen P., Richard Wilcocks, Elizabeth Prosen, Scott Collins, Nolan J. Dewdney, and Yaping Hong. "Acyloin Formation Mediated by Benzoylformate Decarboxylases." In Microbial Reagents in Organic Synthesis, 67–75. Dordrecht: Springer Netherlands, 1992. http://dx.doi.org/10.1007/978-94-011-2444-7_6.

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Grimmett, M. R. "Use of Acyloins and Derivatives." In Five-Membered Hetarenes with Two Nitrogen or Phosphorus Atoms, 1. Georg Thieme Verlag KG, 2002. http://dx.doi.org/10.1055/sos-sd-012-00408.

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"7. Acyloin Condensation." In Organic Chemistry: 100 Must-Know Mechanisms, 26–27. De Gruyter, 2020. http://dx.doi.org/10.1515/9783110608373-007.

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Brettle, Roger. "Acyloin Coupling Reactions." In Comprehensive Organic Synthesis, 613–32. Elsevier, 1991. http://dx.doi.org/10.1016/b978-0-08-052349-1.00074-3.

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Tobe, Y., and T. Takeda. "By Acyloin Condensation." In Monocyclic Arenes, Quasiarenes, and Annulenes, 1. Georg Thieme Verlag KG, 2010. http://dx.doi.org/10.1055/sos-sd-045-01389.

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Scheidt, K. A., and E. A. O'Bryan. "3.12 Acyloin Coupling Reactions." In Comprehensive Organic Synthesis II, 621–55. Elsevier, 2014. http://dx.doi.org/10.1016/b978-0-08-097742-3.00317-7.

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