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Journal articles on the topic 'Corey-Chaykovsky reaction'

Author: Grafiati

Published: 4 June 2021

Last updated: 25 July 2025

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1

Connon, S., S. Kavanagh, and A. Piccinini. "Organocatalytic Corey-Chaykovsky Reaction of Ketones." Synfacts 2010, no. 12 (2010): 1418. http://dx.doi.org/10.1055/s-0030-1258931.

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2

Suchandra, Chakraborty, Basu Kaushik, and Saha Chandan. "Distinction between the reactivity of phosphorus ylide vs sulfur ylide with the carbonyl compounds : Simplicity and logic." Education in Chemical Science and Technology Vol. 2, Aug 2022 (2022): 9–24. https://doi.org/10.5281/zenodo.6813268.

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Department of Clinical and Experimental Pharmacology, School of Tropical Medicine, Kolkata-700 073, India E-mail : cskatichandan@gmail.com Department of Chemistry, St. Paul's Cathedral Mission College, Kolkata-700 009, India Wittig olefination and Corey-Chaykovsky epoxidation of carbonyl compounds are well-documented classical and synthetically useful name reactions which are taught in great details in both undergraduate and post-graduate curricula of organic chemistry. Whilst similar reagents (a phosphorus ylide in Wittig olefination and a sulfur ylide in Corey-Chaykovsky epoxidation) and

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3

Cheng, Bin, Bing Zu, Yuntong Li, et al. "Synthesis of CF3-containing spiro-epoxyoxindoles via the Corey–Chaykovsky reaction of N-alkyl isatins with Ph2S+CH2CF3OTf−." Organic & Biomolecular Chemistry 16, no. 19 (2018): 3564–67. http://dx.doi.org/10.1039/c8ob00602d.

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CF<sub>3</sub>-containing spiro-epoxyoxindoles were successfully prepared via Corey–Chaykovsky reaction of N-alkyl isatins with the ylide generated from Ph<sub>2</sub>S<sup>+</sup>CH<sub>2</sub>CF<sub>3</sub>OTf<sup>−</sup> with almost exclusive diastereoselectivity.

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4

Ciaccio, James A., and Courtney E. Aman. "“Instant Methylide” Modification of the Corey–Chaykovsky Cyclopropanation Reaction." Synthetic Communications 36, no. 10 (2006): 1333–41. http://dx.doi.org/10.1080/00397910500521837.

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5

Suigo, Lorenzo, Giulia Lodigiani, Valentina Straniero, and Ermanno Valoti. "(3-Methylene-2,3-dihydronaphtho[2,3-b][1,4]dioxin-2-yl)methanol." Molbank 2022, no. 4 (2022): M1521. http://dx.doi.org/10.3390/m1521.

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(3-Methylene-2,3-dihydronaphtho[2,3-b][1,4]dioxin-2-yl)methanol was unexpectedly achieved as the main reaction product while applying a standard Johnson–Corey–Chaykovsky procedure to the 2,3-dihydronaphtho[2,3-b][1,4]dioxine-2-carbaldehyde, aiming at obtaining the corresponding epoxide. The structure of the recovered compound was confirmed through NMR and HRMS, the melting point was measured by DSC, and the organic purity was assessed using HPLC. We hypothesized the possible mechanism for the obtainment of this side product, which should involve the opening of the dioxane ring soon after the n

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6

Alfonzo, Edwin, Jesse W. L. Mendoza, and Aaron B. Beeler. "One-pot synthesis of epoxides from benzyl alcohols and aldehydes." Beilstein Journal of Organic Chemistry 14 (September 3, 2018): 2308–12. http://dx.doi.org/10.3762/bjoc.14.205.

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A one-pot synthesis of epoxides from commercially available benzyl alcohols and aldehydes is described. The reaction proceeds through in situ generation of sulfonium salts from benzyl alcohols and their subsequent deprotonation for use in Corey–Chaykovsky epoxidation of aldehydes. The generality of the method is exemplified by the synthesis of 34 epoxides that were made from an array of electronically and sterically varied alcohols and aldehydes.

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7

Ivanova, Olga A., Vitaly V. Shorokhov, Ivan A. Andreev, et al. "Synthesis of 2-[2-(Ethoxymethoxy)phenyl]spiro[cyclopropane-1,2′-indene]-1′,3′-dione." Molbank 2023, no. 1 (2023): M1604. http://dx.doi.org/10.3390/m1604.

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An 1,3-indanedione-derived donor–acceptor cyclopropane, bearing the ethoxymethyl-protected phenolic group at the ortho-position of the donor aryl substituent, has been synthesized using a reaction sequence involving the Knoevenagel condensation of 1,3-indanedione with the corresponding protected salicylaldehyde followed by the Corey–Chaykovsky cyclopropanation of the obtained adduct with dimethylsulfoxonium methylide. The structure of the synthesized cyclopropane was unambiguously proved by single-crystal X-ray diffraction data.

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8

Hajra, Saumen, Sayan Roy, and SK Abu Saleh. "Domino Corey–Chaykovsky Reaction for One-Pot Access to Spirocyclopropyl Oxindoles." Organic Letters 20, no. 15 (2018): 4540–44. http://dx.doi.org/10.1021/acs.orglett.8b01840.

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9

Jamieson, Megan, Nicola Brant, Margaret Brimble, and Daniel Furkert. "Remarkable Influence of Cobalt Catalysis on Epoxide Ring-Opening with Sulfoxonium Ylides." Synthesis 49, no. 17 (2017): 3952–56. http://dx.doi.org/10.1055/s-0036-1588814.

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Cobalt demonstrates a remarkable ability to catalytically divert the course of epoxide to oxetane ring expansion via reaction with a sulfoxonium ylide. An expanded survey of transition-metal catalysts has confirmed that cobalt salts uniquely instead deliver homoallylic alcohol products from epoxides, with retention of the original epoxide stereochemistry. The reaction is an unusual example of cobalt-catalysed epoxide ring-opening by a carbon nucleophile. A tandem Corey–Chaykovsky/epoxide olefination sequence giving homoallylic alcohols from aldehydes is further demonstrated along with prelimi

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10

Mihara, Yurina, Haruki Kadoya, Soki Kakihana, and Naoyuki Kotoku. "Concise and Stereospecific Total Synthesis of Arenastatin A and Its Segment B Analogs." Molecules 29, no. 17 (2024): 4058. http://dx.doi.org/10.3390/molecules29174058.

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A novel and concise synthetic method for arenastatin A, a cytotoxic cyclic depsipeptide of marine origin, was developed in this study. The convergent assembly of the four segments, including the cross-metathesis reaction, gave a cyclization precursor, and Fmoc deprotection caused simultaneous macrocyclization. The Corey–Chaykovsky reaction using a chiral sulfur ylide afforded arenastatin A with complete stereoselectivity in the longest linear sequence of seven reaction steps from the known compound. Using this synthetic method, some analogs of segment B were prepared through a late-stage diver

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11

Lindvall, Mika K., and Ari M. P. Koskinen. "Origins of Stereoselectivity in the Corey−Chaykovsky Reaction. Insights from Quantum Chemistry." Journal of Organic Chemistry 64, no. 13 (1999): 4596–606. http://dx.doi.org/10.1021/jo9818935.

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12

Vaitla, Janakiram, and Annette Bayer. "Sulfoxonium Ylide Derived Metal Carbenoids in Organic Synthesis." Synthesis 51, no. 03 (2018): 612–28. http://dx.doi.org/10.1055/s-0037-1610328.

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As pioneered by Corey and Chaykovsky, sulfoxonium ylides have had widespread application in organic synthesis for more than a half century. In most of the reactions, sulfoxonium ylides were used to react with electrophiles. Under suitable reaction conditions these ylides can generate metal carbenoids and react with nucleophiles. By combining the typical reactivity of sulfoxonium ylides with transition-metal catalysis, a growing number of investigations have expanded their application in organic synthesis. This review provides an update on the preparation of sulfoxonium ylides and their applica

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13

Patel, Kaushalendra, Uttam K. Mishra, Dipto Mukhopadhyay, and S. S. V. Ramasastry. "Beyond the Corey–Chaykovsky Reaction: Synthesis of Unusual Cyclopropanoids via Desymmetrization and Thereof." Chemistry – An Asian Journal 14, no. 24 (2019): 4568–71. http://dx.doi.org/10.1002/asia.201901108.

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14

Peng, Yu, Jin-Hui Yang та Wei-Dong Z. Li. "Revisiting the Corey–Chaykovsky reaction: the solvent effect and the formation of β-hydroxy methylthioethers". Tetrahedron 62, № 6 (2006): 1209–15. http://dx.doi.org/10.1016/j.tet.2005.10.068.

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15

Časar, Zdenko. "Synthetic Approaches to Contemporary Drugs that Contain the Cyclopropyl Moiety." Synthesis 52, no. 09 (2020): 1315–45. http://dx.doi.org/10.1055/s-0039-1690058.

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The U.S. Food and Drug Administration approved 18 new drugs that incorporate the cyclopropyl structural motif in the time frame from 2012 to 2018. This review provides an overview of synthetic approaches to these drugs with emphasis on the construction of the cyclopropyl moiety or its incorporation into the key building blocks for assembly of the highlighted drugs. Based on the structural diversity of these drugs, synthetic approaches for the construction and introduction of the cyclopropyl moiety into their structure are diverse and include: cycloalkylation (double alkylation) of CH-acids, ca

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16

Budynina, Ekaterina M., Konstantin L. Ivanov, Hamidulla B. Tukhtaev, Feruza O. Tukhtaeva, Stanislav I. Bezzubov та Mikhail Ya Melnikov. "One-Pot Synthesis of γ-Azidobutyronitriles and Their Intramolecular Cycloadditions". Synthesis 52, № 22 (2020): 3356–73. http://dx.doi.org/10.1055/s-0040-1706402.

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Efficient gram-scale, one-pot approaches to azidocyanobutyrates and their amidated or decarboxylated derivatives have been developed, starting from commercially available aldehydes and cyanoacetates. These techniques combine (1) Knoevenagel condensation, (2) Corey–Chaykovsky cyclopropanation and (3) nucleophilic ring opening of donor-acceptor cyclopropanes with the azide ion, as well as (4) Krapcho decarboxylation or (4′) amidation. The synthetic utility of the resulting γ-azidonitriles was demonstrated by their transformation into tetrazoles via intramolecular (3+2)-cycloaddition. A condition

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17

Stockman, Robert A., Daniel Morton, David Pearson, and Robert A. Field. "Corey-Chaykovsky Reaction of Chiral Sulfinyl Imines: A Convenient Procedure for the Formation of Chiral Aziridines." Synlett, no. 13 (2003): 1985–88. http://dx.doi.org/10.1055/s-2003-42028.

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18

Akiyama, Hitoshi, Tetsuya Fujimoto, Katsuyoshi Ohshima, Kenji Hoshino, Iwao Yamamoto, and Ryozo Iriye. "Reaction of a Cyclic Oxosulfonium Ylide with Acetates of the Baylis-Hillman Adducts: Tandem Michael−Intramolecular Corey-Chaykovsky Reactions." Organic Letters 1, no. 3 (1999): 427–30. http://dx.doi.org/10.1021/ol990069f.

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19

Buljan, Anđela, Višnja Stepanić, Ana Čikoš, Sanja Babić Brčić, Krunoslav Bojanić, and Marin Roje. "Total Synthesis and Biological Profiling of Putative (±)-Marinoaziridine B and (±)-N-Methyl Marinoaziridine A." Marine Drugs 22, no. 7 (2024): 310. http://dx.doi.org/10.3390/md22070310.

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The total synthesis of two new marine natural products, (±)-marinoaziridine B 7 and (±)-N-methyl marinoaziridine A 8, was accomplished. The (±)-marinoaziridine 7 was prepared in a six-step linear sequence with a 2% overall yield. The key steps in our strategy were the preparation of the chiral epoxide (±)-5 using the Johnson Corey Chaykovsky reaction, followed by the ring-opening reaction and the Staudinger reaction. The N,N-dimethylation of compound (±)-7 gives (±)-N-methyl marinoaziridine A 8. The NMR spectra of synthetized (±)-marinoaziridine B 7 and isolated natural product did not match.

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20

Kumar, B. Senthil, V. Venkataramasubramanian та Arumugam Sudalai. "Organocatalytic Sequential α-Amination/Corey–Chaykovsky Reaction of Aldehydes: A High Yield Synthesis of 4-Hydroxypyrazolidine Derivatives". Organic Letters 14, № 10 (2012): 2468–71. http://dx.doi.org/10.1021/ol300739b.

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21

Sedenkova, Kseniya N., Olga V. Ryzhikova, Svetlana A. Stepanova, et al. "Bis(oxiranes) Containing Cyclooctane Core: Synthesis and Reactivity towards NaN3." Molecules 27, no. 20 (2022): 6889. http://dx.doi.org/10.3390/molecules27206889.

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Reactions of oxirane ring opening provide a powerful tool for regio- and stereoselective synthesis of polyfunctional and heterocyclic compounds, widely used in organic chemistry and drug design. Cyclooctane, alongside other medium-sized rings, is of interest as a novel molecular platform for the construction of target-oriented leads. Additionally, cyclooctane derivatives are well known to be prone to transannular reactions, which makes them a promising object in the search for novel approaches to polycyclic structures. In the present work, a series of cyclooctanediones was studied in Corey-Cha

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22

Volatron, F., and O. Eisenstein. "Wittig versus Corey-Chaykovsky Reaction. Theoretical study of the reactivity of phosphonium methylide and sulfonium methylide with formaldehyde." Journal of the American Chemical Society 109, no. 1 (1987): 1–14. http://dx.doi.org/10.1021/ja00235a001.

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23

Hajra, Saumen, Sk Mohammad Aziz, Bibekananda Jana, Prosenjit Mahish, and Dhiraj Das. "Synthesis of Chiral Spiro-Aziridine Oxindoles via Aza-Corey–Chaykovsky Reaction of Isatin Derived N-tert-Butanesulfinyl Ketimines." Organic Letters 18, no. 3 (2016): 532–35. http://dx.doi.org/10.1021/acs.orglett.5b03564.

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24

Akiyama, Hitoshi, Tetsuya Fujimoto, Katsuyoshi Ohshima, Kenji Hoshino, and Iwao Yamamoto. "ChemInform Abstract: Reaction of a Cyclic Oxosulfonium Ylide with Acetates of the Baylis-Hillman Adducts: Tandem Michael-Intramolecular Corey-Chaykovsky Reactions." ChemInform 30, no. 47 (2010): no. http://dx.doi.org/10.1002/chin.199947105.

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25

Kumar, B. Senthil, V. Venkataramasubramanian та Arumugam Sudalai. "ChemInform Abstract: Organocatalytic Sequential α-Amination/Corey-Chaykovsky Reaction of Aldehydes: A High Yield Synthesis of 4-Hydroxypyrazolidine Derivatives." ChemInform 43, № 38 (2012): no. http://dx.doi.org/10.1002/chin.201238108.

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26

Laali, Kenneth K., Rajesh G. Kalkhambkar, and Suraj M. Sutar. "Recent Advances in the Synthesis of Diverse Libraries of Small-Molecule Building Blocks in Ionic Liquids (ILs)." Synlett 33, no. 07 (2021): 617–36. http://dx.doi.org/10.1055/s-0040-1719852.

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AbstractThe Account describes recent advances, from the authors’ laboratories, in the synthesis of diverse libraries of small-molecule building blocks employing ionic liquids (ILs). The ability of ILs to act as catalysts/promoters/solvents for electrophilic and onium ion chemistry, as well as in metal-mediated cross-coupling reactions, and the potential to sequence/hyphenate these methods, have opened up new opportunities for facile assembly of functional small molecules with increased complexity from readily available precursors. While Brønsted acidic IL/IL solvent mixtures are suitable media

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27

Ohno, Fumihiko, Takayuki Kawashima та Renji Okazaki. "Synthesis, Crystal Structure, and Thermolysis of a Pentacoordinate 1,2λ6-Oxathietane: An Intermediate of the Corey−Chaykovsky Reaction of Oxosulfonium Ylides?" Journal of the American Chemical Society 118, № 3 (1996): 697–98. http://dx.doi.org/10.1021/ja953533u.

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28

Kano, Naokazu, Yuya Daicho, and Takayuki Kawashima. "A Potential Intermediate for the Aza-Corey−Chaykovsky Reaction: Synthesis, Structure, and Thermolysis of a Pentacoordinate 1,2-Thiazetidine 1-Oxide." Organic Letters 8, no. 20 (2006): 4625–27. http://dx.doi.org/10.1021/ol0618499.

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29

Saito, Takao, Masao Sakairi, and Daisuke Akiba. "Enantioselective synthesis of aziridines from imines and alkyl halides using a camphor-derived chiral sulfide mediator via the imino Corey–Chaykovsky reaction." Tetrahedron Letters 42, no. 32 (2001): 5451–54. http://dx.doi.org/10.1016/s0040-4039(01)01016-4.

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30

Saito, Takao, Daisuke Akiba, Masao Sakairi, and Shintaro Kanazawa. "Preparation of a novel, camphor-derived sulfide and its evaluation as a chiral auxiliary mediator in asymmetric epoxidation via the Corey–Chaykovsky reaction." Tetrahedron Letters 42, no. 1 (2001): 57–59. http://dx.doi.org/10.1016/s0040-4039(00)01878-5.

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31

OHNO, F., T. KAWASHIMA, and R. OKAZAKI. "ChemInform Abstract: Synthesis, Crystal Structure, and Thermolysis of a Pentacoordinate 1,2. lambda.6-Oxathietane: An Intermediate of the Corey-Chaykovsky Reaction of Oxosulfonium Ylides?" ChemInform 27, no. 19 (2010): no. http://dx.doi.org/10.1002/chin.199619111.

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32

Saito, Takao, Masao Sakairi, and Daisuke Akiba. "ChemInform Abstract: Enantioselective Synthesis of Aziridines from Imines and Alkyl Halides Using a Camphor-Derived Chiral Sulfide Mediator via the Imino Corey-Chaykovsky Reaction." ChemInform 32, no. 44 (2010): no. http://dx.doi.org/10.1002/chin.200144119.

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33

Saito, Takao, Daisuke Akiba, Masao Sakairi, and Shintaro Kanazawa. "ChemInform Abstract: Preparation of a Novel, Camphor-Derived Sulfide and Its Evaluation as a Chiral Auxiliary Mediator in Asymmetric Epoxidation via the Corey-Chaykovsky Reaction." ChemInform 32, no. 12 (2001): no. http://dx.doi.org/10.1002/chin.200112105.

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34

Fadeev, Alexander A., Anton S. Makarov, Olga A. Ivanova, Maxim G. Uchuskin, and Igor V. Trushkov. "Extended Corey–Chaykovsky reactions: transformation of 2-hydroxychalcones to benzannulated 2,8-dioxabicyclo[3.2.1]octanes and 2,3-dihydrobenzofurans." Organic Chemistry Frontiers 9, no. 3 (2022): 737–44. http://dx.doi.org/10.1039/d1qo01646f.

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35

Chittimalla, Santhosh Kumar, Tsung-Che Chang, Ting-Chun Liu, Hsing-Pang Hsieh, and Chun-Chen Liao. "Reactions of 2-hydroxybenzophenones with Corey–Chaykovsky reagent." Tetrahedron 64, no. 11 (2008): 2586–95. http://dx.doi.org/10.1016/j.tet.2008.01.024.

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36

Kavanagh, Sarah A, Alessandro Piccinini, and Stephen J Connon. "Efficient Catalytic Corey–Chaykovsky Reactions Involving Ketone Substrates." Advanced Synthesis & Catalysis 352, no. 11‐12 (2010): 2089–93. http://dx.doi.org/10.1002/adsc.201000255.

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37

Hommelsheim, Renè, Katharina J. Hock, Christian Schumacher, Mohanad A. Hussein, Thanh V. Nguyen, and Rene M. Koenigs. "Cyanomethyl anion transfer reagents for diastereoselective Corey–Chaykovsky cyclopropanation reactions." Chemical Communications 54, no. 81 (2018): 11439–42. http://dx.doi.org/10.1039/c8cc05602a.

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38

Kavanagh, Sarah A., Alessandro Piccinini, and Stephen J. Connon. "ChemInform Abstract: Efficient Catalytic Corey-Chaykovsky Reactions Involving Ketone Substrates." ChemInform 42, no. 3 (2010): no. http://dx.doi.org/10.1002/chin.201103096.

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39

Hock, Katharina J., Renè Hommelsheim, Lucas Mertens, Junming Ho, Thanh V. Nguyen, and Rene M. Koenigs. "Corey–Chaykovsky Reactions of Nitro Styrenes Enable cis-Configured Trifluoromethyl Cyclopropanes." Journal of Organic Chemistry 82, no. 15 (2017): 8220–27. http://dx.doi.org/10.1021/acs.joc.7b00951.

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40

Nishimura, Yoshio, Takao Shiraishi, and Masahiko Yamaguchi. "(Z)-Selective Wittig and Corey–Chaykovsky reactions of propargyl ylides using trialkylgallium bases." Tetrahedron Letters 49, no. 21 (2008): 3492–95. http://dx.doi.org/10.1016/j.tetlet.2008.03.086.

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41

M. Heravi, Majid, Shima Asadi, Niousha Nazari, and Boshra Malekzadeh Lashkariani. "Developments of Corey-Chaykovsky in Organic Reactions and Total Synthesis of Natural Products." Current Organic Synthesis 13, no. 3 (2016): 308–33. http://dx.doi.org/10.2174/1570179412666150710182304.

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42

O’Shaughnessy, Ciarán, Mukulesh Mondal, and Nessan J. Kerrigan. "Recent Developments in Stereoselective Reactions of Sulfoxonium Ylides." Molecules 30, no. 3 (2025): 655. https://doi.org/10.3390/molecules30030655.

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This review probes the recent developments in stereoselective reactions within the area of sulfoxonium ylide chemistry since the early 2000s. An abundance of research has been applied to sulfoxonium ylide chemistry since its emergence in the early 1960s. There has been a continued effort since then with work in traditional areas, such as epoxidation, aziridination and cyclopropanation. Efforts have also been applied in novel areas, such as olefination and insertion reactions, to develop stereoselective methodologies using organocatalysis and transition metal catalysis. The growing research are

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43

Xiang, Yu, Xing Fan, Pei-Jun Cai, and Zhi-Xiang Yu. "Understanding Regioselectivities of Corey-Chaykovsky Reactions of Dimethylsulfoxonium Methylide (DMSOM) and Dimethylsulfonium Methylide (DMSM) toward Enones: A DFT Study." European Journal of Organic Chemistry 2019, no. 2-3 (2018): 582–90. http://dx.doi.org/10.1002/ejoc.201801216.

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44

Kavanagh, Sarah A., and Stephen J. Connon. "N-Alkyl salts derived from ephedrine do not promote enantioselective Corey–Chaykovsky reactions involving sulfonium methylides under phase-transfer conditions." Tetrahedron: Asymmetry 19, no. 12 (2008): 1414–17. http://dx.doi.org/10.1016/j.tetasy.2008.05.029.

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45

Ghosh, Sunil, Gonna Naidu, and Rekha Singh. "[3]Dendralenes: Synthesis, Reactivity Studies and Employment in Diversity-Oriented Synthesis of Complex Polycyclic Scaffolds." Synlett 29, no. 03 (2017): 282–95. http://dx.doi.org/10.1055/s-0036-1590960.

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[3]Dendralenes are exquisite molecules as they exhibit enormous potential for the rapid generation of architecturally esoteric scaffolds when subjected to tandem Diels–Alder reactions, but their synthesis is a tall order. In conjunction with diversity-oriented synthesis, [3]dendralenes satisfy the potential demand for simultaneous and efficient synthesis of intricate collections of molecules that exhibit a range of activities for lead generation in drug discovery. This account chronicles our roller-coaster journey and systematic approach beginning from the synthesis of extremely unstable, non-

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46

Kotha, Sambasivarao, and Mohammad Salman. "Design and Synthesis of Out/Out, Out/In, and In/In Epoxides in Cage Polycyclic Frameworks." Synlett, August 12, 2024. http://dx.doi.org/10.1055/a-2384-6736.

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We report a useful synthetic approach to assemble In/In epoxide, In/Out epoxide, and Out/Out epoxide in cage systems using Corey–Chaykovsky reaction and Peterson olefination as key steps. In this regard, a variety of pentacycloundecane (PCUD) based cage compounds containing oxirane rings with diverse stereochemical disposition were synthesized via a simple synthetic sequence. Five cage diones were used for this purpose and the starting cage diones were prepared with easily accessible starting materials such as 1,4-hydroquinone derivatives and cyclopentadiene. Here, we have used the Diels–Alder

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47

Yang, Mao-Lin, Hong-Ling Pan, Han-Han Kong, and Ming-Wu Ding. "One-Pot and Divergent Synthesis of Polysubstituted Quinolin-2(1H)-ones and Oxireno[2,3-c]quinolin-2(1aH,3H,7bH)-ones via Sequential Ugi/Knoevenagel Condensation/Hydrolysis and Ugi/Corey-Chaykovsky Epoxidation Reactions." Organic Chemistry Frontiers, 2022. http://dx.doi.org/10.1039/d2qo01130a.

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A new one-pot and divergent synthesis of multisubstituted quinolin-2(1H)-ones and oxireno[2,3-c]quinolin-2(1aH,3H,7bH)-ones via sequential Ugi/Knoevenagel condensation/hydrolysis and Ugi/ Corey-Chaykovsky epoxidation reaction was developed. The four-component reactions of 2-acylanilines, aldehydes, (carboxymethyl)(dimethyl)sulfonium bromides...

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48

Singh, Bara, Arshad Jamal Ansari, Nirmal Malik, and S. S. V. Ramasastry. "An Interrupted Corey-Chaykovsky Reaction of Designed Azaarenium Salts: Synthesis of Complex Polycyclic Spiro- and Fused Cyclopropanoids." Chemical Science, 2023. http://dx.doi.org/10.1039/d3sc01578e.

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Simultaneous dearomatizing spirannulation of pyridinium salts is still in its infancy. Here, we present an organized skeletal remodeling of designed pyridinium salts by utilizing an interrupted Corey-Chaykovsky reaction to access...

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Shi, Hucheng, Guoren Yue, Penji Yan, et al. "A new method for synthesizing terminal olefins from esters using the Corey–Chaykovsky reagent." Organic & Biomolecular Chemistry, 2024. http://dx.doi.org/10.1039/d4ob00620h.

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Abstract:

A new synthetic method for terminal olefins was developed through the reaction of the Corey–Chaykovsky reagent with readily available esters. A mechanism involving nucleophilic addition, elimination and rearrangement is supported by DFT calculations.

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Antoniak, Damian, and Michal Barbasiewicz. "Reactions of Nitroarenes with Corey-Chaykovsky Reagents." Synlett, August 31, 2022. http://dx.doi.org/10.1055/a-1934-1254.

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Abstract:

Electrophilic and nucleophilic substitutions of aromatic substrates share common mechanistic pathways. In both scenarios reacting species attack rings at the unsubstituted (C-H) positions, giving cationic Wheland intermediates, or anionic Meisenheimer complexes. However, the following step of rearomatization breaks the intrinsic symmetry, due to different leaving group ability of proton and hydride anion, respectively. In effect, electron-deficient arenes are prone to transformations unparalleled in electrophilic chemistry. In our article, we present transformations of anionic σH-adducts, form

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