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Journal articles on the topic 'Α-hydroxyketones'

Author: Grafiati

Published: 14 April 2023

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1

Huang, Jinwen, Fanhong Wu, Zhongyuan Li та ін. "Indium-Mediated Reformatsky Reaction of Iododifluoro Ketones with Aldehydes: Preparation of α,α-Difluoro-β-hydroxyketone Derivatives in Water". SynOpen 06, № 01 (2022): 19–30. http://dx.doi.org/10.1055/s-0040-1719888.

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AbstractIndium can efficiently mediate the Reformatsky reaction of iododifluoroacetylketones with aldehydes to afford the corresponding α,α-difluoro-β-hydroxyketones in high yield in pure water This reaction has excellent substrate suitability and functional group selectivity and provides an efficient approach for the synthesis of bioactive molecules containing the α,α-difluoro-β-hydroxyketone pharmacophore.

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2

Kam, Mei Kee, Akira Sugiyama, Ryouta Kawanishi та Kazutaka Shibatomi. "Asymmetric Synthesis of Tertiary α -Hydroxyketones by Enantioselective Decarboxylative Chlorination and Subsequent Nucleophilic Substitution". Molecules 25, № 17 (2020): 3902. http://dx.doi.org/10.3390/molecules25173902.

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Chiral tertiary α-hydroxyketones were synthesized with high enantiopurity by asymmetric decarboxylative chlorination and subsequent nucleophilic substitution. We recently reported the asymmetric decarboxylative chlorination of β-ketocarboxylic acids in the presence of a chiral primary amine catalyst to obtain α-chloroketones with high enantiopurity. Here, we found that nucleophilic substitution of the resulting α-chloroketones with tetrabutylammonium hydroxide yielded the corresponding α-hydroxyketones without loss of enantiopurity. The reaction proceeded smoothly even at a tertiary carbon. Th

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3

Zheng, Shasha, Wietse Smit, Anke Spannenberg, Sergey Tin та Johannes G. de Vries. "Synthesis of α-keto aldehydes via selective Cu(i)-catalyzed oxidation of α-hydroxy ketones". Chemical Communications 58, № 29 (2022): 4639–42. http://dx.doi.org/10.1039/d2cc00773h.

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4

Naveen, Naganaboina, та Rengarajan Balamurugan. "Catalyst free synthesis of α-fluoro-β-hydroxy ketones/α-fluoro-ynols via electrophilic fluorination of tertiary propargyl alcohols using Selectfluor™ (F-TEDA-BF4)". Organic & Biomolecular Chemistry 15, № 9 (2017): 2063–72. http://dx.doi.org/10.1039/c7ob00140a.

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5

Tanaka, Toru, Masami Kawase та Satoru Tani. "α-Hydroxyketones as inhibitors of urease". Bioorganic & Medicinal Chemistry 12, № 2 (2004): 501–5. http://dx.doi.org/10.1016/j.bmc.2003.10.017.

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6

Oelerich, Jens, та Gerard Roelfes. "Alkylidene malonates and α,β-unsaturated α′-hydroxyketones as practical substrates for vinylogous Friedel–Crafts alkylations in water catalysed by scandium(iii) triflate/SDS". Organic & Biomolecular Chemistry 13, № 9 (2015): 2793–99. http://dx.doi.org/10.1039/c4ob02487g.

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7

Tsukamoto, Takashi, Takashi Yamazaki та Tomoya Kitazume. "Enzymic Optical Resolution of α,α-Difluoro-β-Hydroxyketones". Synthetic Communications 20, № 20 (1990): 3181–86. http://dx.doi.org/10.1080/00397919008051543.

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8

Iseki, Katsuhiko, Daisuke Asada та Yoshichika Kuroki. "Preparation of optically active α,α-difluoro-β-hydroxyketones". Journal of Fluorine Chemistry 97, № 1-2 (1999): 85–89. http://dx.doi.org/10.1016/s0022-1139(99)00033-0.

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9

Li, Heng, Nan Liu, Xian Hui, and Wen-Yun Gao. "An improved enzymatic method for the preparation of (R)-phenylacetyl carbinol." RSC Advances 7, no. 52 (2017): 32664–68. http://dx.doi.org/10.1039/c7ra04641c.

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10

Muschallik, Lukas, Denise Molinnus, Melanie Jablonski та ін. "Synthesis of α-hydroxy ketones and vicinal (R,R)-diols by Bacillus clausii DSM 8716T butanediol dehydrogenase". RSC Advances 10, № 21 (2020): 12206–16. http://dx.doi.org/10.1039/d0ra02066d.

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11

Lopp, Margus, Anne Paju, Tõnis Kanger та Tõnis Pehk. "Direct asymmetric α-hydroxylation of β-hydroxyketones". Tetrahedron Letters 38, № 28 (1997): 5051–54. http://dx.doi.org/10.1016/s0040-4039(97)01102-7.

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12

Mitra, Alok Kumar, Aparna De, and Nilay Karchaudhuri. "Microwave-assisted Syntheses of 1,2-Diketones." Journal of Chemical Research 23, no. 3 (1999): 246–47. http://dx.doi.org/10.1177/174751989902300338.

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13

Zhang, Xingxian. "In situ halo-aldol reaction of aldehydes with cyclopropyl ketone promoted by Mgl2 etherate." Journal of Chemical Research 2009, no. 8 (2009): 505–7. http://dx.doi.org/10.3184/030823407x12474221035280.

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14

Volostnykh, Ol'ga G., Olesya A. Shemyakina, Anton V. Stepanov та Igor' A. Ushakov. "Cs₂CO₃-Promoted reaction of tertiary bromopropargylic alcohols and phenols in DMF: a novel approach to α-phenoxyketones". Beilstein Journal of Organic Chemistry 18 (12 квітня 2022): 420–28. http://dx.doi.org/10.3762/bjoc.18.44.

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The reaction of bromopropargylic alcohols with phenols in the presence of Cs2CO3/DMF affords α-phenoxy-α’-hydroxyketones (1:1 adducts) and α,α-diphenoxyketones (1:2 adducts) in up to 92% and 24% yields, respectively. Both products are formed via ring opening of the same intermediates, 1,3-dioxolan-2-ones, generated in situ from bromopropargylic alcohols and Cs2CO3.

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15

Sun, Peipei, та Baochuan Shi. "Tin-mediated Organic Reactions: A Practical Method for the Synthesis of β-Hydroxynitriles and β-Hydroxyketones". Journal of Chemical Research 23, № 5 (1999): 318–19. http://dx.doi.org/10.1177/174751989902300511.

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In the presence of chlorotrimethylsilane, the tin mediated addition of bromoacetonitrile or α-bromacetophenone to aldehydes in THF gives β-hydroxynitriles or β-hydroxyketones in moderate to good yields.

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16

Okada, Hideki, Tomonori Mori, Yoko Saikawa та Masaya Nakata. "Formation of α-hydroxyketones via irregular Wittig reaction". Tetrahedron Letters 50, № 12 (2009): 1276–78. http://dx.doi.org/10.1016/j.tetlet.2008.12.102.

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17

Ghiringhelli, Francesca, Lukas Nattmann, Sabine Bognar та Manuel van Gemmeren. "The Direct Conversion of α-Hydroxyketones to Alkynes". Journal of Organic Chemistry 84, № 2 (2018): 983–93. http://dx.doi.org/10.1021/acs.joc.8b02941.

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18

Iseki, Katsuhiko, Daisuke Asada та Yoshichika Kuroki. "ChemInform Abstract: Preparation of Optically Active α,α-Difluoro-β-hydroxyketones." ChemInform 30, № 43 (2010): no. http://dx.doi.org/10.1002/chin.199943084.

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19

Runcie, Karen A., та Richard J. K. Taylor. "The in situ oxidation–Wittig reaction of α-hydroxyketones". Chemical Communications, № 9 (4 квітня 2002): 974–75. http://dx.doi.org/10.1039/b201513g.

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20

Brown, Herbert C., Mu-Fa Zou та P. Veeraraghavan Ramachandran. "Efficient diastereoselective synthesis of anti-α-bromo-β-hydroxyketones". Tetrahedron Letters 40, № 45 (1999): 7875–77. http://dx.doi.org/10.1016/s0040-4039(99)01640-8.

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21

Amurrio, Iñigo, Ruben Córdoba, Aurelio G. Csákÿ та Joaquín Plumet. "Tetrabutylammonium cyanide catalyzed diasteroselective cyanosilylation of chiral α-hydroxyketones". Tetrahedron 60, № 46 (2004): 10521–24. http://dx.doi.org/10.1016/j.tet.2004.07.101.

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22

Carrera, Ignacio, Margarita C. Brovetto, Juan Carlos Ramos та Gustavo A. Seoane. "Microwave-assisted, solvent-free oxidative cleavage of α-hydroxyketones". Tetrahedron Letters 50, № 38 (2009): 5399–402. http://dx.doi.org/10.1016/j.tetlet.2009.07.048.

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23

Runcie, Karen A., та Richard J. K. Taylor. "The in situ Oxidation-Wittig Reaction of α-Hydroxyketones." ChemInform 33, № 35 (2010): 55. http://dx.doi.org/10.1002/chin.200235055.

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24

LOPP, M., A. PAJU, T. KANGER та T. PEHK. "ChemInform Abstract: Direct Asymmetric α-Hydroxylation of β-Hydroxyketones." ChemInform 28, № 43 (2010): no. http://dx.doi.org/10.1002/chin.199743035.

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25

Patrzałek, Michał, Aleksandra Zasada, Anna Kajetanowicz та Karol Grela. "Tandem Olefin Metathesis/α-Ketohydroxylation Revisited". Catalysts 11, № 6 (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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26

Ohta, Hiromichi, Jin Konishi, Yasuo Kato та Gen-ichi Tsuchihashi. "Microbial Reduction of 1,2-Diketones to Optically Active α-Hydroxyketones". Agricultural and Biological Chemistry 51, № 9 (1987): 2421–27. http://dx.doi.org/10.1080/00021369.1987.10868385.

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27

Corriu, Robert J. P., Gérard F. Lanneau та Zhifang Yu. "Intramolecular nucleophilic catalysis. Stereoselective hydrosilylation of diketones and α-hydroxyketones." Tetrahedron 49, № 40 (1993): 9019–30. http://dx.doi.org/10.1016/s0040-4020(01)91219-0.

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28

Kabalka, George W., Nan-Sheng Li та Su Yu. "Carbonylation of dialkylcyanocuprates with carbon monoxide: Synthesis of α-hydroxyketones". Tetrahedron Letters 38, № 13 (1997): 2203–6. http://dx.doi.org/10.1016/s0040-4039(97)00338-9.

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29

Wong, Fung Fuh, Po-Wei Chang, Hui-Chang Lin, Bang-Jau You, Jiann-Jyh Huang та Shao-Kai Lin. "An efficient and convenient transformation of α-haloketones to α-hydroxyketones using cesium formate". Journal of Organometallic Chemistry 694, № 21 (2009): 3452–55. http://dx.doi.org/10.1016/j.jorganchem.2009.06.031.

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30

Huo, Xiaohong, Rui He, Xiao Zhang та Wanbin Zhang. "An Ir/Zn Dual Catalysis for Enantio- and Diastereodivergent α-Allylation of α-Hydroxyketones". Journal of the American Chemical Society 138, № 35 (2016): 11093–96. http://dx.doi.org/10.1021/jacs.6b06156.

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31

Vu, Nam Duc, Boris Guicheret, Nicolas Duguet, Estelle Métay та Marc Lemaire. "Homogeneous and heterogeneous catalytic (dehydrogenative) oxidation of oleochemical 1,2-diols to α-hydroxyketones". Green Chemistry 19, № 14 (2017): 3390–99. http://dx.doi.org/10.1039/c7gc00867h.

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32

Xia, Mengxin, Mardi Santoso, Ziad Moussa та Zaher M. A. Judeh. "A Concise Synthesis of Pyrrole-Based Drug Candidates from α-Hydroxyketones, 3-Oxobutanenitrile, and Anilines". Molecules 28, № 3 (2023): 1265. http://dx.doi.org/10.3390/molecules28031265.

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A simple and concise three-component synthesis of a key pyrrole framework was developed from the reaction between α-hydroxyketones, oxoacetonitriles, and anilines. The synthesis was used to obtain several pyrrole-based drug candidates, including COX-2 selective NSAID, antituberculosis lead candidates BM212, BM521, and BM533, as well as several analogues. This route has potential to obtain diverse libraries of these pyrrole candidates in a concise manner to develop optimum lead compounds.

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33

Akiba, Kin-ya, Hideyuki Ohnari та Katsuo Ohkata. "OXIDATION OF α-HYDROXYKETONES WITH TRIPHENYLANTIMONY DIBROMIDE AND ITS CATALYTIC CYCLE". Chemistry Letters 14, № 10 (1985): 1577–80. http://dx.doi.org/10.1246/cl.1985.1577.

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34

Streuff, Jan. "An Update on Catalytic Strategies for the Synthesis of α-Hydroxyketones". Synlett 24, № 03 (2012): 276–80. http://dx.doi.org/10.1055/s-0032-1317716.

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35

Kumar, Anil, Ramesh K. Sharma, Tej V. Singh та Paloth Venugopalan. "Indium(III) bromide catalyzed direct azidation of α-hydroxyketones using TMSN3". Tetrahedron 69, № 50 (2013): 10724–32. http://dx.doi.org/10.1016/j.tet.2013.10.055.

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36

Nestl, Bettina M., Anne Bodlenner, Rainer Stuermer, Bernhard Hauer, Wolfgang Kroutil та Kurt Faber. "Biocatalytic racemization of synthetically important functionalized α-hydroxyketones using microbial cells". Tetrahedron: Asymmetry 18, № 12 (2007): 1465–74. http://dx.doi.org/10.1016/j.tetasy.2007.06.005.

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37

Harris, Geraint H., та Andrew E. Graham. "Efficient oxidation-Wittig olefination-Diels–Alder multicomponent reactions of α-hydroxyketones". Tetrahedron Letters 51, № 52 (2010): 6890–92. http://dx.doi.org/10.1016/j.tetlet.2010.10.121.

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38

Tsujigami, Toshikuni, Takeshi Sugai та Hiromichi Ohta. "Microbial asymmetric reduction of α-hydroxyketones in the anti-Prelog selectivity". Tetrahedron: Asymmetry 12, № 18 (2001): 2543–49. http://dx.doi.org/10.1016/s0957-4166(01)00448-7.

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39

Bulman Page, Philip C., Mark Purdie та David Lathbury. "Enantioselective synthesis of α-hydroxyketones using the ditox asymmetric building block". Tetrahedron Letters 37, № 49 (1996): 8929–32. http://dx.doi.org/10.1016/s0040-4039(96)02050-3.

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40

Sato, Satoshi, Ryoji Takahashi, Toshiaki Sodesawa, Hiromitsu Fukuda, Takeshi Sekine та Eriko Tsukuda. "Synthesis of α-hydroxyketones from 1,2-diols over Cu-based catalyst". Catalysis Communications 6, № 9 (2005): 607–10. http://dx.doi.org/10.1016/j.catcom.2005.05.014.

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41

Brown, Herbert C., Mu-Fa Zou та P. Veeraraghavan Ramachandran. "ChemInform Abstract: Efficient Diastereoselective Synthesis of anti-α-Bromo-β-hydroxyketones." ChemInform 31, № 2 (2010): no. http://dx.doi.org/10.1002/chin.200002110.

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42

Wan, Dong-Bei, та Jiang-Min Chen. "Poly{[4-(Hydroxy)(Tosyloxy)Iodo]Styrene}-Promoted Direct α-Hydroxylation of Ketones to α-Hydroxyketones". Journal of Chemical Research 2006, № 1 (2006): 32–33. http://dx.doi.org/10.3184/030823406776331179.

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43

Yan, Jun, Benjamin R. Travis та Babak Borhan. "Direct Oxidative Cleavage of α- and β-Dicarbonyls and α-Hydroxyketones to Diesters with KHSO5". Journal of Organic Chemistry 69, № 26 (2004): 9299–302. http://dx.doi.org/10.1021/jo048665x.

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44

Neuser, Frauke, Holger Zorn та Ralf G. Berger. "Formation of Aliphatic and Aromatic α-Hydroxy Ketones by Zygosaccharomyces bisporus". Zeitschrift für Naturforschung C 55, № 7-8 (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 stro

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45

Xu, Zhi-Hua, Na Li, Zhe-Ran Chang та ін. "Acyl transfer-enabled catalytic asymmetric Michael addition of α-hydroxy-1-indanones to nitroolefins". Chemical Synthesis 3, № 2 (2023): 17. http://dx.doi.org/10.20517/cs.2022.35.

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We report herein an enantioselective acyl transfer protocol via electrophile activation. The reaction cascade sequence encompasses dinuclear zinc-catalyzed asymmetric Michael addition, intramolecular cyclization, and retro-Claisen reaction, which leads to a step- and atom-economic approach to a variety of protected cyclic tertiary α-hydroxyketones in good yields with excellent enantioselectivities (24 examples, 56%-82% yield, 1.5-13 dr and 79%-96% ee). Besides, the large-scale synthesis and further transformation of the products demonstrate the effectiveness of this method for organic synthesi

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46

Kabalka, George W., Nan-Sheng Li та Su Yu. "Synthesis of α,α-dichloroalcohols, α-hydroxyketones and 1-chloro-1-arylalkylene oxides via protonation of acyllithium reagents". Journal of Organometallic Chemistry 572, № 1 (1999): 31–36. http://dx.doi.org/10.1016/s0022-328x(98)00797-9.

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47

Elečko, Pavol, Štefan Toma, Miroslav Vrúbel, and Eva Solčániová. "Reactivity of [m]ferrocenophanones: The aldol condensation." Collection of Czechoslovak Chemical Communications 51, no. 5 (1986): 1112–18. http://dx.doi.org/10.1135/cccc19861112.

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Investigation of the reaction of [m]ferrocenophanones with p-chlorobenzaldehyde in basic medium showed that these cyclic ketones are much more reactive than their acyclic counterparts. The size of the bridge and the position of the carbonyl group influenced the reaction. Thus, [m]ferrocenophan-1-ones (m =3,4 afforded β-hydroxyketones only, [5]ferrocenophan-1-one gave in addition an α,β-unsaturated ketone, and [4]ferrocenophane-2-one yielded only α,β-unsaturated ketones. Oxidation of [m]ferrocenophanes with MnO2 furnished the expected monoketones and [4]ferrocenophane-1,4-dione and [5[ferroceno

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48

Ashraf-Khorassani, Mehdi, William M. Coleman, Michael F. Dube та Larry T. Taylor. "Optimization of α-Hydroxyketone and Pyrazine Syntheses Employing Preliminary Reactions of Glucose and Buffer Solutions". Beiträge zur Tabakforschung International/Contributions to Tobacco Research 28, № 7 (2019): 329–39. http://dx.doi.org/10.2478/cttr-2019-0014.

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SummaryGlucose and selected phosphate buffers have been reacted employing systematic variations in reaction temperature and time (150–160 °C for 60–90 min) to optimize the yield of acetol. This mixture was reacted further with NH4OH, systematically varying reaction conditions and reagent ratios to optimize pyrazine yield. The highest yield of pyrazine was obtained when 1 g of glucose was reacted with 25 mL of buffer at 150–160 °C for 60 min, which in turn was reacted with 1 mL of concentrated aqueous NH4OH at 120–130 °C for 17–18 h. Higher temperatures and higher concentrations of glucose caus

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49

Gatling, Sterling C., та James E. Jackson. "Reactivity Control via Dihydrogen Bonding: Diastereoselection in Borohydride Reductions of α-Hydroxyketones". Journal of the American Chemical Society 121, № 37 (1999): 8655–56. http://dx.doi.org/10.1021/ja991784n.

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50

Andrey, Olivier, Alexandre Alexakis та Gérald Bernardinelli. "Asymmetric Michael Addition of α-Hydroxyketones to Nitroolefins Catalyzed by Chiral Diamine". Organic Letters 5, № 14 (2003): 2559–61. http://dx.doi.org/10.1021/ol0348755.

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