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Journal articles on the topic 'Α-hydroxyketones'

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Author: Grafiati

Published: 14 April 2023

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1

Huang, Jinwen, Fanhong Wu, Zhongyuan Li, Zhuang Ni, Ran Sun, Hui Nie, Hui Tang, and Lixing Song. "Indium-Mediated Reformatsky Reaction of Iododifluoro Ketones with Aldehydes: Preparation of α,α-Difluoro-β-hydroxyketone Derivatives in Water." SynOpen 06, no. 01 (January 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, and Kazutaka Shibatomi. "Asymmetric Synthesis of Tertiary α -Hydroxyketones by Enantioselective Decarboxylative Chlorination and Subsequent Nucleophilic Substitution." Molecules 25, no. 17 (August 27, 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. The proposed method would be useful for the preparation of chiral tertiary alcohols.

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3

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

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4

Naveen, Naganaboina, and 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, no. 9 (2017): 2063–72. http://dx.doi.org/10.1039/c7ob00140a.

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5

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

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6

Oelerich, Jens, and 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, no. 9 (2015): 2793–99. http://dx.doi.org/10.1039/c4ob02487g.

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7

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

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8

Iseki, Katsuhiko, Daisuke Asada, and Yoshichika Kuroki. "Preparation of optically active α,α-difluoro-β-hydroxyketones." Journal of Fluorine Chemistry 97, no. 1-2 (July 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, Carina Ronja Kipp, Johannes Bongaerts, Martina Pohl, Torsten Wagner, Michael J. Schöning, Thorsten Selmer, and Petra Siegert. "Synthesis of α-hydroxy ketones and vicinal (R,R)-diols by Bacillus clausii DSM 8716T butanediol dehydrogenase." RSC Advances 10, no. 21 (2020): 12206–16. http://dx.doi.org/10.1039/d0ra02066d.

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11

Lopp, Margus, Anne Paju, Tõnis Kanger, and Tõnis Pehk. "Direct asymmetric α-hydroxylation of β-hydroxyketones." Tetrahedron Letters 38, no. 28 (July 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 (March 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 (August 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, and 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 (April 12, 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, and Baochuan Shi. "Tin-mediated Organic Reactions: A Practical Method for the Synthesis of β-Hydroxynitriles and β-Hydroxyketones." Journal of Chemical Research 23, no. 5 (May 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, and Masaya Nakata. "Formation of α-hydroxyketones via irregular Wittig reaction." Tetrahedron Letters 50, no. 12 (March 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, and Manuel van Gemmeren. "The Direct Conversion of α-Hydroxyketones to Alkynes." Journal of Organic Chemistry 84, no. 2 (December 19, 2018): 983–93. http://dx.doi.org/10.1021/acs.joc.8b02941.

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18

Iseki, Katsuhiko, Daisuke Asada, and Yoshichika Kuroki. "ChemInform Abstract: Preparation of Optically Active α,α-Difluoro-β-hydroxyketones." ChemInform 30, no. 43 (June 13, 2010): no. http://dx.doi.org/10.1002/chin.199943084.

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19

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

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20

Brown, Herbert C., Mu-Fa Zou, and P. Veeraraghavan Ramachandran. "Efficient diastereoselective synthesis of anti-α-bromo-β-hydroxyketones." Tetrahedron Letters 40, no. 45 (November 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, and Joaquín Plumet. "Tetrabutylammonium cyanide catalyzed diasteroselective cyanosilylation of chiral α-hydroxyketones." Tetrahedron 60, no. 46 (November 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, and Gustavo A. Seoane. "Microwave-assisted, solvent-free oxidative cleavage of α-hydroxyketones." Tetrahedron Letters 50, no. 38 (September 2009): 5399–402. http://dx.doi.org/10.1016/j.tetlet.2009.07.048.

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23

Runcie, Karen A., and Richard J. K. Taylor. "The in situ Oxidation-Wittig Reaction of α-Hydroxyketones." ChemInform 33, no. 35 (May 20, 2010): 55. http://dx.doi.org/10.1002/chin.200235055.

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24

LOPP, M., A. PAJU, T. KANGER, and T. PEHK. "ChemInform Abstract: Direct Asymmetric α-Hydroxylation of β-Hydroxyketones." ChemInform 28, no. 43 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199743035.

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25

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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26

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

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27

Corriu, Robert J. P., Gérard F. Lanneau, and Zhifang Yu. "Intramolecular nucleophilic catalysis. Stereoselective hydrosilylation of diketones and α-hydroxyketones." Tetrahedron 49, no. 40 (January 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, and Su Yu. "Carbonylation of dialkylcyanocuprates with carbon monoxide: Synthesis of α-hydroxyketones." Tetrahedron Letters 38, no. 13 (March 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, and Shao-Kai Lin. "An efficient and convenient transformation of α-haloketones to α-hydroxyketones using cesium formate." Journal of Organometallic Chemistry 694, no. 21 (October 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, and Wanbin Zhang. "An Ir/Zn Dual Catalysis for Enantio- and Diastereodivergent α-Allylation of α-Hydroxyketones." Journal of the American Chemical Society 138, no. 35 (August 25, 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, and Marc Lemaire. "Homogeneous and heterogeneous catalytic (dehydrogenative) oxidation of oleochemical 1,2-diols to α-hydroxyketones." Green Chemistry 19, no. 14 (2017): 3390–99. http://dx.doi.org/10.1039/c7gc00867h.

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32

Xia, Mengxin, Mardi Santoso, Ziad Moussa, and Zaher M. A. Judeh. "A Concise Synthesis of Pyrrole-Based Drug Candidates from α-Hydroxyketones, 3-Oxobutanenitrile, and Anilines." Molecules 28, no. 3 (January 28, 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, and Katsuo Ohkata. "OXIDATION OF α-HYDROXYKETONES WITH TRIPHENYLANTIMONY DIBROMIDE AND ITS CATALYTIC CYCLE." Chemistry Letters 14, no. 10 (October 5, 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, no. 03 (December 10, 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, and Paloth Venugopalan. "Indium(III) bromide catalyzed direct azidation of α-hydroxyketones using TMSN3." Tetrahedron 69, no. 50 (December 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, and Kurt Faber. "Biocatalytic racemization of synthetically important functionalized α-hydroxyketones using microbial cells." Tetrahedron: Asymmetry 18, no. 12 (July 2007): 1465–74. http://dx.doi.org/10.1016/j.tetasy.2007.06.005.

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37

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

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38

Tsujigami, Toshikuni, Takeshi Sugai, and Hiromichi Ohta. "Microbial asymmetric reduction of α-hydroxyketones in the anti-Prelog selectivity." Tetrahedron: Asymmetry 12, no. 18 (October 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, and David Lathbury. "Enantioselective synthesis of α-hydroxyketones using the ditox asymmetric building block." Tetrahedron Letters 37, no. 49 (December 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, and Eriko Tsukuda. "Synthesis of α-hydroxyketones from 1,2-diols over Cu-based catalyst." Catalysis Communications 6, no. 9 (September 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, and P. Veeraraghavan Ramachandran. "ChemInform Abstract: Efficient Diastereoselective Synthesis of anti-α-Bromo-β-hydroxyketones." ChemInform 31, no. 2 (June 11, 2010): no. http://dx.doi.org/10.1002/chin.200002110.

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42

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

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43

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

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44

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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45

Xu, Zhi-Hua, Na Li, Zhe-Ran Chang, Yuan-Zhao Hua, Li-Ping Xu, Shi-Kun Jia, Min-Can Wang, and Guang-Jian Mei. "Acyl transfer-enabled catalytic asymmetric Michael addition of α-hydroxy-1-indanones to nitroolefins." Chemical Synthesis 3, no. 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 synthesis.

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46

Kabalka, George W., Nan-Sheng Li, and 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, no. 1 (January 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[ferrocenophane-1,2-dione. The preparation of [5]ferrocenophane-1,5-dione was also improved.

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48

Ashraf-Khorassani, Mehdi, William M. Coleman, Michael F. Dube, and 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, no. 7 (December 1, 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 caused a decrease in the yield of pyrazines. The addition of hydrolyzed tobacco-derived F1 protein as a secondary source of nitrogen increased the yield of pyrazines by 2–10% depending on F1 protein concentration. Furthermore, the addition of any α-hydroxyketone, similar in structure to acetol, as a pure reagent to the reaction mixture not only increased the yields of pyrazine by ranging from 25–100 % depending on the reagent concentration, but also significantly altered the qualitative and quantitative distribution of the pyrazines. With all of the reaction parameters examined (reaction time, temperature, reagent ratios, etc.) the most significant impacts on both pyrazine yield and distribution were noted when: 1) glucose was pre-reacted with buffer, 2) hydrolyzed F1 protein was added as a second nitrogen source, and 3) when pure α-hydroxyketones were employed as co-reagents. Use of these reaction parameters was found to dramatically shift the pyrazine distribution toward higher molecular weight resulting in a pyrazine array having more desirable physical and sensory attributes.

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49

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

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50

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

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