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Journal articles on the topic 'Alkylation of ketoester'

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Published: 5 June 2025

Last updated: 1 August 2025

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1

Gravel, Denis, та Marc Labelle. "The γ-alkylation of cyclic β-ketoesters via their enamine derivatives". Canadian Journal of Chemistry 63, № 7 (1985): 1874–83. http://dx.doi.org/10.1139/v85-311.

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The γ-alkylation – functionalization of cyclic β-ketoesters via their enamine derivatives is discussed with particular emphasis on their preparation from β-ketoesters and their reaction with various electrophiles such as electrophilic olefins, halogenoïds, and allylic and benzylic halides. Although the amine ring size does not appear to affect reactivity to a great extent, the reaction is very sensitive to β-ketoester ring size, with six-membered rings giving the best results. In the latter case the alkylation–functionalization is general and specific to the γ-position and therefore provides a

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2

Hodgson, David M., and Hasanain A. A. Almohseni. "Evolution of a Cycloaddition–Rearrangement Approach to the Squalestatins: A Quarter-Century Odyssey." Synlett 31, no. 16 (2020): 1555–72. http://dx.doi.org/10.1055/s-0040-1707127.

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The highs, lows, and diversions of a journey leading to two syntheses of 6,7-dideoxysqualestatin H5 is described. Both syntheses relied on highly diastereoselective n-alkylations of a tartrate acetonide enolate and subsequent oxidation–hydrolysis to provide an asymmetric entry to β-hydroxy-α-ketoester motifs. The latter were differentially elaborated to diazoketones which underwent stereo- and regioselective Rh(II)-catalysed cyclic carbonyl ylide formation–cycloaddition and then acid-catalysed transketalisation to generate the 2,8-dioxabicyclo[3.2.1]octane core of the squalestatins/zaragozic a

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3

Parimal, K. Sen, Das Tulika, Maiti Krishnasri, Maiti Basudeb, and K. Sarkar Achintya. "Studies on alkylation of Hagemann's ester and its derivatives with alkyl halides and Michael acceptors." Journal of Indian Chemical Society Vol. 76, Nov-Dec 1999 (1999): 583–87. https://doi.org/10.5281/zenodo.5862213.

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Department of Chemistry, Presidency College, Calcutta-700 073, India <em>Manuscript received 25 August 1999</em> Alkylation and Michael addition of ethyl 3-methyl-4-oxo-2-phenylcyclohex-2-enecarboxylate (1b) have been studied under basic conditions. Similar reactions with Hagemann's ester (1c) have been carried out using phase transfer catalysts as well as solid supports. The ratio of the C-1 to C-3 alkylated products have been determined. A probable explanation for the regioselectivity observed has been given.

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4

Nanney, Dylan R., and Richard A. Bunce. "Methyl 12-Methyl-3,9-dinitro-5,6,7,12-tetrahydro-13-oxodibenzo[b.g]bicyclo[3.3.1]nonane-6-carboxylate and Related Compounds." Molbank 2022, no. 4 (2022): M1526. http://dx.doi.org/10.3390/m1526.

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A synthesis of the title compound and related structures is reported. The procedure involves double alkylation of a β-ketoester followed by double SNAr ring closure from the γ carbon to give a dibenzo[3.3.1]bicyclic unit. This paper appears to be the first to generate a mid-sized bicyclic target by a double SNAr process. The synthesis can be performed in one step, but yields are superior (52–62%) when a two-stage procedure is used.

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5

Fennie, Michael W., Erin F. DiMauro, Erin M. O'Brien, Venkatachalam Annamalai та Marisa C. Kozlowski. "Mechanism and scope of salen bifunctional catalysts in asymmetric aldehyde and α-ketoester alkylation". Tetrahedron 61, № 26 (2005): 6249–65. http://dx.doi.org/10.1016/j.tet.2005.03.117.

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6

Pickersgill, I. Fraser, Allan P. Marchington та Christopher M. Rayner. "Selective alkylation of β-ketoester enolates using O-methyl aminosulfoxonium salts; the first example of C-alkylation using sulfoxonium salt electrophiles". J. Chem. Soc., Chem. Commun., № 22 (1994): 2597–98. http://dx.doi.org/10.1039/c39940002597.

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7

Lavallée, Jean-François, та Pierre Deslongchamps. "Synthesis of tricyclic compounds via sequential intramolecular Michael addition and alkylation of β-ketoester ynones". Tetrahedron Letters 28, № 30 (1987): 3457–58. http://dx.doi.org/10.1016/s0040-4039(00)96325-1.

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8

PICKERSGILL, I. F., A. P. MARCHINGTON та C. M. RAYNER. "ChemInform Abstract: Selective Alkylation of β-Ketoester Enolates Using O-Methyl Aminosulfoxonium Salts; The First Example of C-Alkylation Using Sulfoxonium Salt Electrophiles." ChemInform 26, № 17 (2010): no. http://dx.doi.org/10.1002/chin.199517071.

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9

Krylova, E. S., V. E. Semenov, V. D. Akamsin, and V. S. Reznik. "Condensation of thiourea with uracyl derivatives containing ketone and ketoester fragments, alkylation and macrocyclization of the condensation products." Russian Journal of General Chemistry 80, no. 7 (2010): 1364–68. http://dx.doi.org/10.1134/s107036321007025x.

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10

Mizota, Isao, Miki Maeda, Kiho Imoto та Makoto Shimizu. "Synthesis of Tetramic Acid Derivatives via a Tandem Umpolung Alkylation/Reduction/Cyclization Reaction of γ-Hydrazono β-Ketoester". Organic Letters 22, № 8 (2020): 3079–83. http://dx.doi.org/10.1021/acs.orglett.0c00824.

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11

Trost, Barry M., Robert N. Bream та Jiayi Xu. "Asymmetric Allylic Alkylation of Cyclic Vinylogous Esters and Thioesters by Pd-Catalyzed Decarboxylation of Enol Carbonate and β-Ketoester Substrates". Angewandte Chemie 118, № 19 (2006): 3181–84. http://dx.doi.org/10.1002/ange.200504421.

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12

Trost, Barry M., Robert N. Bream та Jiayi Xu. "Asymmetric Allylic Alkylation of Cyclic Vinylogous Esters and Thioesters by Pd-Catalyzed Decarboxylation of Enol Carbonate and β-Ketoester Substrates". Angewandte Chemie International Edition 45, № 19 (2006): 3109–12. http://dx.doi.org/10.1002/anie.200504421.

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13

Aikawa, Kohsuke, Kazuya Honda, Shunsuke Mimura та Koichi Mikami. "Highly enantioselective Friedel–Crafts alkylation of indole and pyrrole with β,γ-unsaturated α-ketoester catalyzed by chiral dicationic palladium complex". Tetrahedron Letters 52, № 50 (2011): 6682–86. http://dx.doi.org/10.1016/j.tetlet.2011.09.006.

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14

Aikawa, Kohsuke, Kazuya Honda, Shunsuke Mimura та Koichi Mikami. "ChemInform Abstract: Highly Enantioselective Friedel-Crafts Alkylation of Indole and Pyrrole with β,γ-Unsaturated α-Ketoester Catalyzed by Chiral Dicationic Palladium Complex." ChemInform 43, № 15 (2012): no. http://dx.doi.org/10.1002/chin.201215103.

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15

Ma, Hong-Li, Jia-Qi Li, Lu Sun, Xu-He Hou, Zhen-Hua Zhang та Bin Fu. "Heteroarylidene-tethered bis(oxazoline) copper complexes catalyzed cascade reaction involving asymmetric Friedel–Crafts alkylation/N-hemiacetalization of indoles with β,γ-unsaturated α-ketoester". Tetrahedron 71, № 22 (2015): 3625–31. http://dx.doi.org/10.1016/j.tet.2014.12.020.

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16

Clariana, Jaume, Santiago Garcı́a-Granda, Vicente Gotor та ін. "Preparation of (R)-(1-adamantyl)glycine and (R)-2-(1-adamantyl)-2-aminoethanol: a combination of cobalt-mediated β-ketoester alkylation and enzyme-based aminoalcohol resolution". Tetrahedron: Asymmetry 11, № 22 (2000): 4549–57. http://dx.doi.org/10.1016/s0957-4166(00)00428-6.

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17

Ma, Hong-Li, Jia-Qi Li, Lu Sun, Xu-He Hou, Zhen-Hua Zhang та Bin Fu. "ChemInform Abstract: Heteroarylidene-Tethered Bis(oxazoline) Copper Complexes Catalyzed Cascade Reaction Involving Asymmetric Friedel-Crafts Alkylation/N-Hemiacetalization of Indoles with β,γ-Unsaturated α-Ketoester." ChemInform 46, № 37 (2015): no. http://dx.doi.org/10.1002/chin.201537150.

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18

Yamanaka, Masahiro, Masamitsu Inaba, Ryo Gotoh, Yoshiyuki Ueki та Kenichiro Matsui. "Multinuclear zinc bisamidinate catalyzed asymmetric alkylation of α-ketoesters and its unique chemoselectivity". Chemical Communications 53, № 54 (2017): 7513–16. http://dx.doi.org/10.1039/c7cc01736g.

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19

Inanaga, Kazato, Marco Wollenburg, Shoshana Bachman, Nicholas J. Hafeman, and Brian M. Stoltz. "Catalytic enantioselective synthesis of carbocyclic and heterocyclic spiranes via a decarboxylative aldol cyclization." Chemical Science 11, no. 28 (2020): 7390–95. http://dx.doi.org/10.1039/d0sc02366c.

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20

Trost, Barry M., Rumen Radinov та Ellen M. Grenzer. "Asymmetric Alkylation of β-Ketoesters". Journal of the American Chemical Society 119, № 33 (1997): 7879–80. http://dx.doi.org/10.1021/ja971523i.

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21

Surya Prakash Rao, H., K. Subba Reddy та S. N. Balasubrahmanyam. "Stereoselections in cyclic β-ketoester alkylations". Tetrahedron Letters 35, № 11 (1994): 1759–62. http://dx.doi.org/10.1016/0040-4039(94)88339-4.

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22

TROST, B. M., R. RADINOV та E. M. GRENZER. "ChemInform Abstract: Asymmetric Alkylation of β-Ketoesters." ChemInform 28, № 49 (2010): no. http://dx.doi.org/10.1002/chin.199749038.

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23

Xue, Aiqi, Xingfu Wei, Yue Huang, Jingping Qu, and Baomin Wang. "Palladium-Catalyzed Stereoselective Construction of 1,3-Stereocenters Displaying Axial and Central Chirality via Asymmetric Alkylations." Molecules 28, no. 7 (2023): 2927. http://dx.doi.org/10.3390/molecules28072927.

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The concurrent construction of 1,3-stereocenters remains a challenge. Herein, we report the development of stereoselective union of a point chiral center with allenyl axial chirality in 1,3-position by Pd-catalyzed asymmetric allenylic alkylation between racemic allenyl carbonates and indanone-derived β-ketoesters. Various target products bearing a broad range of functional groups were afforded in high yield (up to 99%) with excellent enantioselectivities (up to 98% ee) and good diastereoselectivities (up to 13:1 dr).

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24

Rajesh, Kancherla, Bandapalli Palakshi Reddy, and Vijayaparthasarathi Vijayakumar. "Novel bipodal, tripodal, and tetrapodal 1,4-dihydropyridines — Microwave-assisted synthesis and structural confinements." Canadian Journal of Chemistry 89, no. 10 (2011): 1236–44. http://dx.doi.org/10.1139/v11-088.

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The one pot, three component reaction of p-hydroxy benzaldehyde, β-ketoester, and ammonium acetate afforded the corresponding monopodal 1,4-dihydropyridines as building blocks, which in turn converted into diversified novel bipodal, tripodal, and tetrapodal 1,4-dihydropyridines with different alkylating agents through conventional as well as microwave assisted reactions. The unambiguous structural confinements of the all the synthesized compounds were drawn out with the help of 2D NMR (H-H COSY and C-H COSY).

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25

RAO, H. S. P., K. S. REDDY та S. N. BALASUBRAHMANYAM. "ChemInform Abstract: Stereoselections in Cyclic β-Ketoester Alkylations." ChemInform 25, № 34 (2010): no. http://dx.doi.org/10.1002/chin.199434125.

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26

Zhou, Jing, Lijuan Bai, Guojuan Liang, et al. "Organocatalytic asymmetric domino Michael/O-alkylation reaction for the construction of succinimide substituted 3(2H)-furanones catalyzed by quinine." RSC Advances 7, no. 63 (2017): 39885–88. http://dx.doi.org/10.1039/c7ra07317h.

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27

Ma, Sandy, Corey M. Reeves, Robert A. Craig та Brian M. Stoltz. "Palladium-catalyzed decarboxylative allylic alkylation of diastereomeric β-ketoesters". Tetrahedron 70, № 27-28 (2014): 4208–12. http://dx.doi.org/10.1016/j.tet.2014.03.042.

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28

Mane, Ramchandra B., Uday V. Desai, and Geeta D. Hebbalkar. "Synthesis of juvabione analogues." Collection of Czechoslovak Chemical Communications 53, no. 3 (1988): 646–57. http://dx.doi.org/10.1135/cccc19880646.

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Alkylation of various β-ketoesters IIIa - d with bis(p-methoxycarbonylphenyl)bromomethane (II) and bis(p-chlorophenyl)bromomethane (VI) followed by cleavage of ethoxycarbonyl group or hydrolysis and esterification gave methoxycarbonylphenyl and chlorophenyl analogues of ar-juvabione, respectively. Condensation of bis(p-methoxycarbonylphenyl)methanol (IX) with isovaleryl and trichloroacetyl chloride gave isovalerate X and trichloroacetate XI, respectively, while the condensation of bis(p-chlorophenyl)methanol (XII) with isovaleryl chloride and citronellyl bromide yielded isovalerate XIII and ci

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29

Audier, H. E., D. Berthomieu, P. Hudhomme, C. Monteiro та P. Mourgues. "Alkylation of esters and β-ketoesters in the gas phase". Organic Mass Spectrometry 25, № 1 (1990): 87–88. http://dx.doi.org/10.1002/oms.1210250119.

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30

Ma, Sandy, Corey M. Reeves, Robert A. Craig та Brian M. Stoltz. "ChemInform Abstract: Palladium-Catalyzed Decarboxylative Allylic Alkylation of Diastereomeric β-Ketoesters." ChemInform 45, № 44 (2014): no. http://dx.doi.org/10.1002/chin.201444052.

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31

DiMauro, Erin F., та Marisa C. Kozlowski. "Development of Bifunctional Salen Catalysts: Rapid, Chemoselective Alkylations of α-Ketoesters". Journal of the American Chemical Society 124, № 43 (2002): 12668–69. http://dx.doi.org/10.1021/ja026498h.

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32

Liu, Wen-Bo, Corey M. Reeves та Brian M. Stoltz. "Enantio-, Diastereo-, and Regioselective Iridium-Catalyzed Asymmetric Allylic Alkylation of Acyclic β-Ketoesters". Journal of the American Chemical Society 135, № 46 (2013): 17298–301. http://dx.doi.org/10.1021/ja4097829.

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33

Trost, Barry M., Benjamin Schäffner, Maksim Osipov та Donna A. A. Wilton. "Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation of β-ketoesters: An Unusual Counterion Effect". Angewandte Chemie International Edition 50, № 15 (2011): 3548–51. http://dx.doi.org/10.1002/anie.201007803.

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34

Trost, Barry M., Benjamin Schäffner, Maksim Osipov та Donna A. A. Wilton. "Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation of β-ketoesters: An Unusual Counterion Effect". Angewandte Chemie 123, № 15 (2011): 3610–13. http://dx.doi.org/10.1002/ange.201007803.

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35

Liu, Wen-Bo, Noriko Okamoto, Eric J. Alexy, Allen Y. Hong, Kristy Tran та Brian M. Stoltz. "Enantioselective γ-Alkylation of α,β-Unsaturated Malonates and Ketoesters by a Sequential Ir-Catalyzed Asymmetric Allylic Alkylation/Cope Rearrangement". Journal of the American Chemical Society 138, № 16 (2016): 5234–37. http://dx.doi.org/10.1021/jacs.6b02153.

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36

Kita, Yusuke, Rahul D. Kavthe, Hiroaki Oda та Kazushi Mashima. "Asymmetric Allylic Alkylation of β-Ketoesters with Allylic Alcohols by a Nickel/Diphosphine Catalyst". Angewandte Chemie International Edition 55, № 3 (2015): 1098–101. http://dx.doi.org/10.1002/anie.201508757.

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37

Kita, Yusuke, Rahul D. Kavthe, Hiroaki Oda та Kazushi Mashima. "Asymmetric Allylic Alkylation of β-Ketoesters with Allylic Alcohols by a Nickel/Diphosphine Catalyst". Angewandte Chemie 128, № 3 (2015): 1110–13. http://dx.doi.org/10.1002/ange.201508757.

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38

Wang, Jia-Xin, Wei Ge, Wei-Long Xing та Ming-Chen Fu. "Photoinduced Deaminative Alkylation for the Synthesis of γ-Ketoesters via Electron Donor–Acceptor Complex Formation". Journal of Organic Chemistry 86, № 24 (2021): 18224–31. http://dx.doi.org/10.1021/acs.joc.1c02499.

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39

Deng, Qing-Hai, Hubert Wadepohl та Lutz H. Gade. "Highly Enantioselective Copper-Catalyzed Alkylation of β-Ketoesters and Subsequent Cyclization to Spirolactones/Bi-spirolactones". Journal of the American Chemical Society 134, № 6 (2012): 2946–49. http://dx.doi.org/10.1021/ja211859w.

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40

Liu, Wen-Bo, Corey M. Reeves та Brian M. Stoltz. "ChemInform Abstract: Enantio-, Diastereo-, and Regioselective Iridium-Catalyzed Asymmetric Allylic Alkylation of Acyclic β-Ketoesters." ChemInform 45, № 23 (2014): no. http://dx.doi.org/10.1002/chin.201423028.

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41

Martín, Nazario, Angeles Martínez-Grau, Carlos Seoane та José L. Marco. "Asymmetric alkylation of β-ketoesters: Synthesis and Michael additions of a chiral sultam-derived acetoacetyl equivalent". Tetrahedron Letters 34, № 35 (1993): 5627–30. http://dx.doi.org/10.1016/s0040-4039(00)73900-1.

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42

Funabashi, Ken, Markus Jachmann, Motomu Kanai та Masakatsu Shibasaki. "Multicenter Strategy for the Development of Catalytic Enantioselective Nucleophilic Alkylation of Ketones: Me2Zn Addition toα-Ketoesters". Angewandte Chemie International Edition 42, № 44 (2003): 5489–92. http://dx.doi.org/10.1002/anie.200351650.

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43

Funabashi, Ken, Markus Jachmann, Motomu Kanai та Masakatsu Shibasaki. "Multicenter Strategy for the Development of Catalytic Enantioselective Nucleophilic Alkylation of Ketones: Me2Zn Addition toα-Ketoesters". Angewandte Chemie 115, № 44 (2003): 5647–50. http://dx.doi.org/10.1002/ange.200351650.

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44

Shakhmaev, Rinat N., Alisa Sh Sunagatullina, Regina M. Alieva та Vladimir V. Zorin. "STEREODIRECTED SYNTHESIS OF (Е)- AND (Z)-ISOMERS OF 8-CHLOROOCT-7-EN-4-ONE". IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENIY KHIMIYA KHIMICHESKAYA TEKHNOLOGIYA 60, № 1 (2017): 40. http://dx.doi.org/10.6060/tcct.2017601.5353.

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For citation:Shakhmaev R.N., Sunagatullina A.Sh., Alieva R.M., Zorin V.V. Stereodirected synthesis of (Е)- and (Z)-isomers of 8-chlorooct-7-en-4-one. Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 2017. V. 60. N 1. P. 40-44. Reaction of ethyl 3-oxohexanoate with equimolar amounts of (E)- or (Z)-1,3-dichloro-propene under phase transfer catalysis conditions in the presence of K2CO3 afforded the corresponding monosubstituted (E)- or (Z)-isomers of ethyl 2-(3- chloroprop-2-en-1-yl)-3-oxohexa-noate and considerable amount of disubstituted derivatives (30-40%). In order to increase yields of monos

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45

Blay, Gonzalo, Isabel Fernández, M. Carmen Muñoz, José R. Pedro, Alejandro Recuenco та Carlos Vila. "Enantioselective Synthesis of Tertiary Alcohols through a Zirconium-Catalyzed Friedel–Crafts Alkylation of Pyrroles with α-Ketoesters". Journal of Organic Chemistry 76, № 15 (2011): 6286–94. http://dx.doi.org/10.1021/jo2010704.

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46

Deng, Qing-Hai, Hubert Wadepohl та Lutz H. Gade. "ChemInform Abstract: Highly Enantioselective Copper-Catalyzed Alkylation of β-Ketoesters and Subsequent Cyclization to Spirolactones/Bi-spirolactones." ChemInform 43, № 29 (2012): no. http://dx.doi.org/10.1002/chin.201229022.

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47

Wang, Shifang, Xiaowei Liu, Dongsheng Zhu та Mang Wang. "Copper-Catalyzed Ring-Opening Defluorinative Alkylation of Siloxydifluorocyclopropanes: Synthesis of γ-Fluoro-δ-Ketoesters and γ,δ-Diketonitriles". Journal of Organic Chemistry 85, № 19 (2020): 12408–17. http://dx.doi.org/10.1021/acs.joc.0c01643.

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48

Zhu, Fu-Lin, Yuan Zou, De-Yang Zhang та ін. "Enantioselective Copper-Catalyzed Decarboxylative Propargylic Alkylation of Propargyl β-Ketoesters with a Chiral Ketimine P,N,N-Ligand". Angewandte Chemie 126, № 5 (2013): 1434–38. http://dx.doi.org/10.1002/ange.201309182.

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49

Jensen, Kim B., Jacob Thorhauge, Rita G. Hazell та Karl Anker Jørgensen. "Catalytic Asymmetric Friedel–Crafts Alkylation ofβ,γ-Unsaturatedα-Ketoesters: Enantioselective Addition of Aromatic C−H Bonds to Alkenes". Angewandte Chemie 113, № 1 (2001): 164–67. http://dx.doi.org/10.1002/1521-3757(20010105)113:1<164::aid-ange164>3.0.co;2-v.

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50

Zhu, Fu-Lin, Yuan Zou, De-Yang Zhang та ін. "Enantioselective Copper-Catalyzed Decarboxylative Propargylic Alkylation of Propargyl β-Ketoesters with a Chiral Ketimine P,N,N-Ligand". Angewandte Chemie International Edition 53, № 5 (2013): 1410–14. http://dx.doi.org/10.1002/anie.201309182.

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