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Journal articles on the topic 'Acyloins'

Author: Grafiati

Published: 4 June 2021

Last updated: 3 February 2022

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1

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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2

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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3

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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4

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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5

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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6

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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7

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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8

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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9

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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10

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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11

Zeynizadeh, Behzad, and Saiedeh Yahyaei. "Ultrasound-Promoted Reduction of Conjugated Enones, α-Diketones and Acyloins with NaBH4 under Aprotic Condition." Zeitschrift für Naturforschung B 59, no. 6 (June 1, 2004): 699–703. http://dx.doi.org/10.1515/znb-2004-0611.

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A variety of conjugated enones are reduced regioselectively to their corresponding allylic alcohols with NaBH4 under ultrasound irradiation. Reduction reactions were performed in THF at room temperature and the product alcohols were obtained in high to excellent yields. This system is also efficient for the reduction of α-diketones and acyloins to vicinal diols.

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12

Zeynizadeh, Behzad, and Tarifeh Behyar. "NaBH4/NaHSO4·H2O a Heterogeneous Acidic System for a Mild and Convenient Reduction of Carbonyl Compounds under Protic Condition." Zeitschrift für Naturforschung B 60, no. 4 (April 1, 2005): 453–57. http://dx.doi.org/10.1515/znb-2005-0417.

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NaBH4 in the presence of sodium bisulfate (NaHSO4·H2O), a weakly acidic reagent, efficiently reduces a variety of carbonyl compounds such as aldehydes, ketones, α,β -unsaturated aldehydes and ketones, α-diketones and acyloins to their corresponding alcohols in acetonitrile under heterogeneous condition. Reduction reactions were accomplished at room temperature or under reflux condition

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13

Uranga, Jorge G., Antonella F. Chiosso, and Ana N. Santiago. "One-step selective deoxygenation of alcohols from acyloins." RSC Advances 3, no. 29 (2013): 11493. http://dx.doi.org/10.1039/c3ra40343b.

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14

Marples, Brian A., and Christopher D. Spilling. "Facile intramolecular ene reactions of steroidal unsaturated acyloins." Tetrahedron 48, no. 19 (January 1992): 4017–26. http://dx.doi.org/10.1016/s0040-4020(01)88481-7.

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15

Setamdideh, Davood, and Mostafa Rafigh. "Reduction of Carbonyl Compounds to Their Corresponding Alcohols by (Nicotine)(tetrahydroborato)zinc Complex as a New Stable and Efficient Reducing Agent." E-Journal of Chemistry 9, no. 4 (2012): 2338–45. http://dx.doi.org/10.1155/2012/391643.

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(Nicotine)(tetrahydroborato)zinc complex, [Zn(BH4)2(nic)], as a stable yellow solid, was prepared quantitatively by complexation of an equimolar amounts of zinc tetrahydroborate and Nicotine at room temperature. This reagent can easily reduce variety of carbonyl compounds such as aldehydes, ketones, acyloins and α-diketones to their corresponding alcohols in good to excellent yields. Reduction reactions were performed in CH3CN at room temperature.

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16

Brussee, J., E. C. Roos, and A. Van Der Gen. "Bio-organic synthesis of optically active cyanohydrins and acyloins." Tetrahedron Letters 29, no. 35 (January 1988): 4485–88. http://dx.doi.org/10.1016/s0040-4039(00)80529-8.

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17

Casajus, Hubert, Aurélie Lagarde, Martin Leremboure, Thomas De Dios Miguel, Lionel Nauton, Vincent Thery, Wolf‐Dieter Fessner, Nicolas Duguet, Franck Charmantray, and Laurence Hecquet. "Enzymatic Synthesis of Aliphatic Acyloins Catalyzed by Thermostable Transketolase." ChemCatChem 12, no. 22 (September 9, 2020): 5772–79. http://dx.doi.org/10.1002/cctc.202001160.

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18

Shirini, F., H. Tajik, A. Aliakbar, and A. Akbar. "OXIDATION OF BENZYL ALCOHOLS AND ACYLOINS WITH (NO3)3CeBrO3." Synthetic Communications 31, no. 5 (January 2001): 767–70. http://dx.doi.org/10.1081/scc-100103267.

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19

Setamdideh, Davood, and Behzad Zeynizadeh. "Mild and Convenient Method for Reduction of Carbonyl Compounds with the NaBH4/Charcoal System in Wet THF." Zeitschrift für Naturforschung B 61, no. 10 (October 1, 2006): 1275–81. http://dx.doi.org/10.1515/znb-2006-1014.

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The NaBH4/C (charcoal) system reduces a variety of carbonyl compounds such as aldehydes, ketones, acyloins and α-diketones to their corresponding alcohols in high to excellent yields. Reduction reactions were carried out in wet THF at r. t. In addition, regioselective 1,2-reduction of α,β - unsaturated aldehydes and ketones was achieved perfectly with this reducing system. By decreasing the amount of aprotic solvent, all reductions took place fast and efficiently under solid-gel condition

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20

Schieferdecker, Sebastian, Gulimila Shabuer, Anne-Catrin Letzel, Barbara Urbansky, Mie Ishida-Ito, Keishi Ishida, Michael Cyrulies, Hans-Martin Dahse, Sacha Pidot, and Christian Hertweck. "Biosynthesis of Diverse Antimicrobial and Antiproliferative Acyloins in Anaerobic Bacteria." ACS Chemical Biology 14, no. 7 (June 5, 2019): 1490–97. http://dx.doi.org/10.1021/acschembio.9b00228.

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21

Sun, Li-Jun, and Shu-Jian Shi. "The Synthesis and PMR Spectra of Alkyl Acyloins of Ferrocene." Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry 19, no. 3 (March 1989): 207–18. http://dx.doi.org/10.1080/00945718908048064.

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22

Plietker, Bernd. "Alkenes as Ketol Surrogates−A New Approach toward Enantiopure Acyloins." Organic Letters 6, no. 2 (January 2004): 289–91. http://dx.doi.org/10.1021/ol0362663.

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23

Kim, Yong Boon, Chung Soo Kim, and Chang Kiu Lee. "Condensation reactions of aryl acyloins with ureas in ethylene glycol." Journal of Heterocyclic Chemistry 31, no. 6 (November 1994): 1653–56. http://dx.doi.org/10.1002/jhet.5570310663.

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24

MARPLES, B. A., and C. D. SPILLING. "ChemInform Abstract: Facile Intramolecular Ene Reactions of Steroidal Unsaturated Acyloins." ChemInform 23, no. 37 (August 21, 2010): no. http://dx.doi.org/10.1002/chin.199237278.

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25

Setamdideh, Davood, Behrooz Khezri, and Mehdi Rahmatollahzadeh. "Zn(BH4)2/Al2O3: A new synthetic method for efficient and convenient reduction of organic carbonyl compounds to their corresponding alcohols." Journal of the Serbian Chemical Society 78, no. 1 (2013): 1–13. http://dx.doi.org/10.2298/jsc120111044s.

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Zn(BH4)2 (0.5-2 mmol) in the presence of Al2O3 (1 mmol) reduces varieties of organic carbonyl compounds such as aldehydes, ketones, acyloins, ?-diketones and ?, ?-unsaturated carbonyl compounds to their corresponding alcohols. Reduction reactions were carried out in THF at room temperature in high to excellent yields of products. The chemoselective reduction of aldehydes over ketones was accomplished successfully with this reducing system. In addition, regioselectivity and exclusive 1,2-reduction of conjugated carbonyl compounds to their corresponding allylic alcohols in high to excellent yields was accomplished successfully with this reducing system.

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26

Kawase, Masami, Hiroshi Sakagami, Kaoru Kusama, Noboru Motohashi, and Setsuo Saito. "α-Trifluoromethylated acyloins induce apoptosis in human oral tumor cell lines." Bioorganic & Medicinal Chemistry Letters 9, no. 21 (November 1999): 3113–18. http://dx.doi.org/10.1016/s0960-894x(99)00548-x.

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27

Rieck, Matthias, Monika Hagen, Sabine Lutz, and Wilfried A. König. "Enantiomer separation of acyloins and cyanohydrins by enantioselective capillary gas chromatography." Journal of Chromatography A 439, no. 2 (January 1988): 301–6. http://dx.doi.org/10.1016/s0021-9673(01)83842-5.

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28

Bornemann, Stephen, David H. G. Crout, Howard Dalton, Vladim�r Kren, Mario Lobell, Gregory Dean, Nicholas Thomson, and Margaret M. Turner. "Stereospecific formation of R-aromatic acyloins by Zymomonas mobilis pyruvate decarboxylase." Journal of the Chemical Society, Perkin Transactions 1, no. 5 (1996): 425. http://dx.doi.org/10.1039/p19960000425.

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29

Sanz‐Marco, Amparo, Samuel Martinez‐Erro, and Belén Martín‐Matute. "Selective Synthesis of Unsymmetrical Aliphatic Acyloins through Oxidation of Iridium Enolates." Chemistry – A European Journal 24, no. 45 (July 18, 2018): 11564–67. http://dx.doi.org/10.1002/chem.201803117.

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30

Feng, Jun-Cai, Qing-Hua Meng, Yang Liu, and Li Dai. "CONDENSATION REACTION OF ACYLOINS WITH UREA WITHOUT SOLVENT UNDER MICROWAVE IRRADIATION." Organic Preparations and Procedures International 29, no. 6 (December 1997): 687–89. http://dx.doi.org/10.1080/00304949709355249.

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31

Shirini, F., H. Tajik, A. Aliakbar, and A. Akbar. "ChemInform Abstract: Oxidation of Benzyl Alcohols and Acyloins with (NO3)3CeBrO3." ChemInform 32, no. 34 (May 25, 2010): no. http://dx.doi.org/10.1002/chin.200134059.

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32

Scheid, Günther, Wouter Kuit, Eelco Ruijter, Romano V. A. Orru, Erik Henke, Uwe Bornscheuer, and Ludger A. Wessjohann. "A New Route to Protected Acyloins and Their Enzymatic Resolution with Lipases." European Journal of Organic Chemistry 2004, no. 5 (March 2004): 1063–74. http://dx.doi.org/10.1002/ejoc.200300338.

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33

Park, Jin-Soo, Noritaka Kagaya, Junko Hashimoto, Miho Izumikawa, Shuhei Yabe, Kazuo Shin-ya, Makoto Nishiyama, and Tomohisa Kuzuyama. "Identification and Biosynthesis of New Acyloins from the Thermophilic BacteriumThermosporothrix hazakensisSK20-1T." ChemBioChem 15, no. 4 (January 28, 2014): 527–32. http://dx.doi.org/10.1002/cbic.201300690.

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34

KIM, Y. B., C. S. KIM, and C. K. LEE. "ChemInform Abstract: Condensation Reactions of Aryl Acyloins with Ureas in Ethylene Glycol." ChemInform 26, no. 22 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199522142.

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35

Křen, Vladimír, David H. G. Grout, Howard Dalton, David W. Hutchinson, Wilfred König, Margaret M. Turner, Gregory Dean, and Nicholas Thomson. "Pyruvate decarboxylase: a new enzyme for the production of acyloins by biotransformation." J. Chem. Soc., Chem. Commun., no. 4 (1993): 341–43. http://dx.doi.org/10.1039/c39930000341.

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36

BORNEMANN, S., D. H. G. CROUT, H. DALTON, V. KREN, M. LOBELL, G. DEAN, N. THOMSON, and M. M. TURNER. "ChemInform Abstract: Stereospecific Formation of R-Aromatic Acyloins by Zymomonas mobilis Pyruvate Decarboxylase." ChemInform 27, no. 24 (August 5, 2010): no. http://dx.doi.org/10.1002/chin.199624061.

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37

FENG, J. C., Q. H. MENG, Y. LIU, and L. DAI. "ChemInform Abstract: Condensation Reaction of Acyloins with Urea Without Solvent under Microwave Irradiation." ChemInform 29, no. 10 (June 23, 2010): no. http://dx.doi.org/10.1002/chin.199810140.

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38

KAWASE, Masami, Setsuo SAITO, and Teruo KURIHARA. "Convenient Synthesis of .ALPHA.-Trifluoromethylated Acyloins from .ALPHA.-Hydroxy or .ALPHA.-Amino Acids." CHEMICAL & PHARMACEUTICAL BULLETIN 48, no. 9 (2000): 1338–43. http://dx.doi.org/10.1248/cpb.48.1338.

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39

Agudo, Rubén, Gheorghe-Doru Roiban, Richard Lonsdale, Adriana Ilie, and Manfred T. Reetz. "Biocatalytic Route to Chiral Acyloins: P450-Catalyzed Regio- and Enantioselective α-Hydroxylation of Ketones." Journal of Organic Chemistry 80, no. 2 (December 23, 2014): 950–56. http://dx.doi.org/10.1021/jo502397s.

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40

KREN, V., D. H. G. CROUT, H. DALTON, D. W. HUTCHINSON, W. KOENIG, M. M. TURNER, G. DEAN, and N. THOMSON. "ChemInform Abstract: Pyruvate Decarboxylase: A New Enzyme for the Production of Acyloins by Biotransformation." ChemInform 24, no. 23 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199323074.

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41

Christoffers, Jens, Thomas Werner, Sven Unger, and Wolfgang Frey. "Preparation of Acyloins by Cerium-Catalyzed, Direct Hydroxylation ofβ-Dicarbonyl Compounds with Molecular Oxygen." European Journal of Organic Chemistry 2003, no. 3 (February 2003): 425–31. http://dx.doi.org/10.1002/ejoc.200390075.

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42

Nestl, Bettina M, Wolfgang Kroutil, and Kurt Faber. "Biocatalytic Racemization of α-Hydroxy Ketones (Acyloins) at Physiological Conditions usingLactobacillus paracasei DSM 20207." Advanced Synthesis & Catalysis 348, no. 7-8 (May 2006): 873–76. http://dx.doi.org/10.1002/adsc.200606055.

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43

Khan, Faiz Ahmed, Jyotirmayee Dash, Nilam Sahu, and Sharad Gupta. "Regio- and Diastereoselective Reduction of Nonenolizable α-Diketones to Acyloins Mediated by Indium Metal." Organic Letters 4, no. 6 (March 2002): 1015–18. http://dx.doi.org/10.1021/ol025593s.

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44

Gacem, B., and G. Jenner. "Effect of pressure on stetter reactions: synthesis of hindered aliphatic acyloins and γ-ketonitriles." High Pressure Research 24, no. 2 (June 2004): 233–36. http://dx.doi.org/10.1080/08957950410001699809.

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45

Kawase, Masami, and Teruo Kurihara. "A convenient synthesis of α-trifluoremethylated and α-perfluoroalkylated acyloins from α-hydroxy acids." Tetrahedron Letters 35, no. 44 (October 1994): 8209–12. http://dx.doi.org/10.1016/0040-4039(94)88284-3.

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46

Prieto, Jose A., Gerald L. Larson, and Patricia Gonzalez. "The Stereochemistry of the Reaction of α-Silyl Lithium Reagents with Cyclic Tert-butyldimethylsilyl Acyloins." Synthetic Communications 19, no. 15 (September 1989): 2773–78. http://dx.doi.org/10.1080/00397918908053073.

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47

Inokuchi, Tsutomu, Hiroyuki Kawafuchi, and Sigeru Torii. "Removal of α-Hydroxy Group of Acyloins and Their Derivatives with Vanadium(II)-THF Complex." Chemistry Letters 21, no. 10 (October 1992): 1895–96. http://dx.doi.org/10.1246/cl.1992.1895.

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48

Winkler, Christoph K., Clemens Stueckler, Nicole J. Mueller, Desiree Pressnitz, and Kurt Faber. "Asymmetric Synthesis of O-Protected Acyloins Using Enoate Reductases: Stereochemical Control through Protecting Group Modification." European Journal of Organic Chemistry 2010, no. 33 (September 28, 2010): 6354–58. http://dx.doi.org/10.1002/ejoc.201001042.

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49

Kawase, Masami, Setsuo Saito, and Teruo Kurihara. "ChemInform Abstract: Convenient Synthesis of α-Trifluoromethylated Acyloins from α-Hydroxy or α-Amino Acids." ChemInform 32, no. 5 (January 30, 2001): no. http://dx.doi.org/10.1002/chin.200105080.

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50

Kahn, Bruce E., and Reuben D. Rieke. "A novel reducing agent. The reduction of dicarbonyls, acyloins, alkynes, and alkenes with active uranium." Journal of Organometallic Chemistry 346, no. 3 (June 1988): C45—C48. http://dx.doi.org/10.1016/0022-328x(88)80144-x.

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