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Journal articles on the topic 'Enolate reactivity'

Author: Grafiati

Published: 4 June 2021

Last updated: 2 February 2022

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1

Ullah, Zakir, та Renjith Thomas. "Mechanistic insights can resolve the low reactivity and selectivity issues in intermolecular Rauhut–Currier (RC) reaction of γ-hydroxyenone". New Journal of Chemistry 44, № 29 (2020): 12857–65. http://dx.doi.org/10.1039/d0nj02732d.

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2

Leonov, Artem, Daria Timofeeva, Armin Ofial, and Herbert Mayr. "Metal Enolates – Enamines – Enol Ethers: How Do Enolate Equivalents Differ in Nucleophilic Reactivity?" Synthesis 51, no. 05 (2019): 1157–70. http://dx.doi.org/10.1055/s-0037-1611634.

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The kinetics of the reactions of trimethylsilyl enol ethers and enamines (derived from deoxybenzoin, indane-1-one, and α-tetralone) with reference electrophiles (p-quinone methides, benzhydrylium and indolylbenzylium ions) were measured by conventional and stopped-flow photometry in acetonitrile at 20 °C. The resulting second-order rate constants were subjected to a least-squares minimization based on the correlation equation lg k = s N(N + E) for determining the reactivity descriptors N and s N of the silyl enol ethers and enamines. The relative reactivities of structurally analogous silyl en

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3

Hare, Michael C., Sudha S. Marimanikkuppam, and Steven R. Kass. "Acetamide enolate: formation, reactivity, and proton affinity." International Journal of Mass Spectrometry 210-211 (September 2001): 153–63. http://dx.doi.org/10.1016/s1387-3806(01)00397-9.

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4

Freriks, Ivo L., Leo J. De Koning, and Nico M. M. Nibbering. "Gas-phase ambident reactivity of acyclic enolate anions." Journal of the American Chemical Society 113, no. 24 (1991): 9119–24. http://dx.doi.org/10.1021/ja00024a014.

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5

Freriks, Ivo L., Leo J. de Koning, and Nico M. M. Nibbering. "Gas-phase ambident reactivity of cyclic enolate anions." Journal of Physical Organic Chemistry 5, no. 11 (1992): 776–82. http://dx.doi.org/10.1002/poc.610051111.

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6

Freriks, Ivo L., Leo J. De Koning, and Nico M. M. Nibbering. "Gas-phase ambident reactivity of monohydrated enolate anions." Journal of Organic Chemistry 57, no. 22 (1992): 5976–79. http://dx.doi.org/10.1021/jo00048a035.

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7

Yatham, Veera Reddy, Jörg-M. Neudörfl, Nils E. Schlörer та Albrecht Berkessel. "Carbene catalyzed umpolung of α,β-enals: a reactivity study of diamino dienols vs. azolium enolates, and the characterization of advanced reaction intermediates". Chemical Science 6, № 7 (2015): 3706–11. http://dx.doi.org/10.1039/c5sc01027f.

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8

Loughlin, Wendy A. "A Facile Approach to Bicyclo[n.2.0]alkan-1-ols: An Overview." Australian Journal of Chemistry 57, no. 4 (2004): 335. http://dx.doi.org/10.1071/ch03213.

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Bicyclo[n.2.0]alkan-1-ols are an integral part of various frameworks of natural products. The reaction of the lithium enolates of simple ketones with (±)-phenyl vinyl sulfoxide and the controlled formation of bicyclo[n.2.0]alkan-1-ols was investigated. Facile access to bicyclo[n.2.0]alkan-1-ols (n = 3–6) bearing a bridgehead hydroxyl group was obtained. The ratio of bicyclo[n.2.0]alkan-1-ols (n = 3–6) to alkyated ketone was found to be dependent on enolate reactivity, electrophile conversion, time, reaction temperature, concentration, as well as the stability and steric strain observed in the

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9

Cativiela, Carlos, Maria Dolores Diaz-De-Villegas, and José Antonio Galvez. "Chiral 2-acetamidoacrylates in conjugate addition – asymmetric enolate trapping reactions. Asymmetric synthesis of phenylalanine." Canadian Journal of Chemistry 70, no. 9 (1992): 2325–28. http://dx.doi.org/10.1139/v92-294.

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A new route to the asymmetric synthesis of α-amino acids based on the reactivity of chiral 2-acetamidoacrylates with nucleophiles through a conjugate addition followed by diastereoselective protonation of the enolate is described. Phenylalanine precursors are obtained in excellent chemical yields (80–95%) with moderate diastereomeric excess (0–44%) through the reaction of chiral 2-acetamidoacrylates with phenylmagnesium bromide in the presence of CuI followed by diastereoselective enolate protonation.

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10

Gualandi, Andrea, Luca Mengozzi, and Pier Cozzi. "Stereoselective SN1-Type Reaction of Enols and Enolates." Synthesis 49, no. 15 (2017): 3433–43. http://dx.doi.org/10.1055/s-0036-1588871.

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Stereoselective alkylation of enolates represents a valuable and important procedure for accessing carbon–carbon-bond frameworks in natural and nonnatural product synthesis. Usually, activated electrophilic partners that react through an SN2 mechanism are employed. To overcome the limitations due to reduced reactivity and steric hindrance, SN1-type reactions can be considered a valid and practical alternative. Accessible enolates can be used in stereoselective (diastereo- or enantioselective) reactions with electrophilic carbenium ions, either used as stable reagents or generated in situ from

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11

Chen, Yi-Hung, Mario Ellwart, Vladimir Malakhov, and Paul Knochel. "Solid Organozinc Pivalates: A New Class of Zinc Organometallics with Greatly Enhanced Air- and Moisture-Stability." Synthesis 49, no. 15 (2017): 3215–23. http://dx.doi.org/10.1055/s-0036-1588843.

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Organozinc species are powerful reagents for performing carbon–carbon and carbon–heteroatom bond-forming reactions in the presence of a transition-metal catalyst. However, extended applications of zinc reagents have been hampered by their moderate air- and moisture-stability. This short review presents our recent developments on the preparation of solid aryl, benzyl, heteroaryl, allyl zinc pivalates and zinc amide enolate reagents with greatly enhanced stability toward to air and moisture.1 Introduction2 Preparation of Organozinc Pivalates2.1 Using Organic Halides as Substrates2.2 Using a Dir

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12

Cámpora, Juan, Celia M. Maya, Pilar Palma, Ernesto Carmona, Enrique Gutiérrez-Puebla, and Caridad Ruiz. "Synthesis and Aldol Reactivity ofO- andC-Enolate Complexes of Nickel." Journal of the American Chemical Society 125, no. 6 (2003): 1482–83. http://dx.doi.org/10.1021/ja028711f.

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13

FRERIKS, I. L., L. J. DE KONING, and N. M. M. NIBBERING. "ChemInform Abstract: Gas-Phase Ambident Reactivity of Acyclic Enolate Anions." ChemInform 23, no. 11 (2010): no. http://dx.doi.org/10.1002/chin.199211093.

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14

Freriks, Ivo L., Leo J. de Koning, and Nico M. M. Nibbering. "Gas-phase reactivity of ambident thio-enolate and oximate anions." Rapid Communications in Mass Spectrometry 7, no. 8 (1993): 757–62. http://dx.doi.org/10.1002/rcm.1290070815.

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15

Kobayashi, Shū, and Satoshi Nagayama. "Aldehydes vs Aldimines. Unprecedented Reactivity in Their Enolate Addition Reactions." Journal of Organic Chemistry 62, no. 2 (1997): 232–33. http://dx.doi.org/10.1021/jo962010h.

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16

Wang, Daniel Zerong, та Andrew Streitwieser. "Aggregation and Reactivity of the Cesium Enolate of 6-Phenyl-α-tetralone: Comparison with the Lithium Enolate1". Journal of Organic Chemistry 68, № 23 (2003): 8936–42. http://dx.doi.org/10.1021/jo034543d.

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17

Buncel, Erwin, Julian M. Dust, and Richard A. Manderville. "Ambident Reactivity of Enolate Ions toward 1,3,5-Trinitrobenzene. The First Observation of an Oxygen-Bonded Enolate Meisenheimer Complex." Journal of the American Chemical Society 118, no. 25 (1996): 6072–73. http://dx.doi.org/10.1021/ja960590u.

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18

Ketz, Benjamin E., Adam P. Cole, and Robert M. Waymouth. "Structure and Reactivity of an Allylpalladium N-Heterocyclic Carbene Enolate Complex." Organometallics 23, no. 12 (2004): 2835–37. http://dx.doi.org/10.1021/om049838b.

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19

Rigby, James H., and Terry L. Moore. "Synthetic studies on ingenol. Bridgehead enolate reactivity and ABC ring assembly." Journal of Organic Chemistry 55, no. 9 (1990): 2959–62. http://dx.doi.org/10.1021/jo00296a075.

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20

Streitwieser, Andrew, James A. Krom, Kathleen V. Kilway, and Alessandro Abbotto. "Aggregation and Reactivity of the Cesium Enolate ofp-Phenylisobutyrophenone in Tetrahydrofuran1." Journal of the American Chemical Society 120, no. 42 (1998): 10801–6. http://dx.doi.org/10.1021/ja981437y.

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21

Magnus, Philip, David Parry, Theodore Iliadis, Shane A. Eisenbeis, and Robin A. Fairhurst. "Short synthesis of the dynemicin core structure: unusual bridgehead enolate reactivity." Journal of the Chemical Society, Chemical Communications, no. 13 (1994): 1543. http://dx.doi.org/10.1039/c39940001543.

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22

Alonso, Ruben A., Carlos H. Rodriguez, and Roberto A. Rossi. "Reactivity of N,N-dialkylamide enolate ions. Arylation of 1-methyl-2-pyrrolidinone enolate ions by the SRN1 mechanism." Journal of Organic Chemistry 54, no. 25 (1989): 5983–85. http://dx.doi.org/10.1021/jo00286a035.

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23

Kolonko, Kristopher J., Daniel J. Wherritt, and Hans J. Reich. "Mechanistic Studies of the Lithium Enolate of 4-Fluoroacetophenone: Rapid-Injection NMR Study of Enolate Formation, Dynamics, and Aldol Reactivity." Journal of the American Chemical Society 133, no. 42 (2011): 16774–77. http://dx.doi.org/10.1021/ja207218f.

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24

Jiang, Wen, Li-Jun Zhang, and Li-Xin Zhang. "Synthesis, Structure, and Reactivity of Monoguanidinate Rare-Earth Metal Aminobenzyl Enolate Complexes." European Journal of Inorganic Chemistry 2020, no. 22 (2020): 2153–64. http://dx.doi.org/10.1002/ejic.202000148.

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25

Benson, Stefan, Bridgett Payne, and Robert M. Waymouth. "Synthesis and reactivity of allyl nickel(II)N-heterocyclic carbene enolate complexes." Journal of Polymer Science Part A: Polymer Chemistry 45, no. 16 (2007): 3637–47. http://dx.doi.org/10.1002/pola.22113.

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26

Meyer, Matthew M, George N Khairallah, Steven R Kass, and Richard A J. O'Hair. "Gas-Phase Synthesis and Reactivity of the Lithium Acetate Enolate Anion, −CH2CO2Li." Angewandte Chemie International Edition 48, no. 16 (2009): 2934–36. http://dx.doi.org/10.1002/anie.200900245.

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27

Huang, Zheng, та John F. Hartwig. "Copper(I) Enolate Complexes in α-Arylation Reactions: Synthesis, Reactivity, and Mechanism". Angewandte Chemie 124, № 4 (2011): 1052–56. http://dx.doi.org/10.1002/ange.201106719.

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28

Meyer, Matthew M, George N Khairallah, Steven R Kass, and Richard A J. O'Hair. "Gas-Phase Synthesis and Reactivity of the Lithium Acetate Enolate Anion,−CH2CO2Li." Angewandte Chemie 121, no. 16 (2009): 2978–80. http://dx.doi.org/10.1002/ange.200900245.

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29

KOBAYASHI, S., and S. NAGAYAMA. "ChemInform Abstract: Aldehydes vs Aldimines. Unprecedented Reactivity in Their Enolate Addition Reactions." ChemInform 28, no. 23 (2010): no. http://dx.doi.org/10.1002/chin.199723051.

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30

Huang, Zheng, та John F. Hartwig. "Copper(I) Enolate Complexes in α-Arylation Reactions: Synthesis, Reactivity, and Mechanism". Angewandte Chemie International Edition 51, № 4 (2011): 1028–32. http://dx.doi.org/10.1002/anie.201106719.

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31

Smith, Andrew, James Douglas, and Gwydion Churchill. "NHCs in Asymmetric Organocatalysis: Recent Advances in Azolium Enolate Generation and Reactivity." Synthesis 44, no. 15 (2012): 2295–309. http://dx.doi.org/10.1055/s-0031-1289788.

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32

Streitwieser, Andrew, and Daniel Ze-Rong Wang. "Aggregation and Reactivity of the Lithium Enolate of 2-Biphenylylcyclohexanone in Tetrahydrofuran1." Journal of the American Chemical Society 121, no. 26 (1999): 6213–19. http://dx.doi.org/10.1021/ja990593h.

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33

Mukaijo, Yusuke, Soichi Yokoyama, and Nagatoshi Nishiwaki. "Comparison of Substituting Ability of Nitronate versus Enolate for Direct Substitution of a Nitro Group." Molecules 25, no. 9 (2020): 2048. http://dx.doi.org/10.3390/molecules25092048.

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α-Nitrocinnamate underwent the conjugate addition of an active methylene compound such as nitroacetate, 1,3-dicarbonyl compound, or α-nitroketone, and the following ring closure afforded functionalized heterocyclic frameworks. The reaction of cinnamate with nitroacetate occurs via nucleophilic substitution of a nitro group by the O-attack of the nitronate, which results in isoxazoline N-oxide. This protocol was applicable to 1,3-dicarbonyl compounds to afford dihydrofuran derivatives, including those derived from direct substitution of a nitro group caused by O-attack of enolate. It was found

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34

Leung, Simon Shun-Wang, and Andrew Streitwieser. "Effect of Addends on Aggregation and Reactivity of the Lithium Enolate ofp-Phenylisobutyrophenone1." Journal of Organic Chemistry 64, no. 10 (1999): 3390–91. http://dx.doi.org/10.1021/jo990075p.

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35

MAGNUS, P., D. PARRY, T. ILIADIS, S. A. EISENBEIS, and R. A. FAIRHURST. "ChemInform Abstract: Short Synthesis of the Dynemicin Core Structure: Unusual Bridgehead Enolate Reactivity." ChemInform 25, no. 47 (2010): no. http://dx.doi.org/10.1002/chin.199447275.

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36

Adams, Alan D., R. H. Schlessinger, J. R. Tata, and J. J. Venit. "The structure and kinetic reactivity of a pyrrolidine-derived vinylogous urethane lithium enolate." Journal of Organic Chemistry 51, no. 15 (1986): 3068–70. http://dx.doi.org/10.1021/jo00365a045.

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37

Kawafuchi, Hiroyuki, Lijian Ma, Md Imran Hossain, and Tsutomu Inokuchi. "O-AcylTEMPOs, a Modified and Fundamental, but Unexplored Carboxylic Derivative: Recent Progress in Synthetic Applications." Current Organic Chemistry 23, no. 19 (2019): 2102–21. http://dx.doi.org/10.2174/1385272823666191019102511.

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O-Acylated 2,2,6,6-tetramethylpiperidine-N-oxyls (abbr. O-AcylTEMPOs) are easily available and stable carboxylic derivatives, but their utility in organic synthesis is unexplored in contrast to analogues, such as the N-methoxy-N-methylamides, known as Weinreb amides. Especially, the O–N unit of the O-acylTEMPOs dictates a fairly electronwithdrawing character for the carbonyl function. This enhances the reactivity and stability of the resulting enolate ions. Accordingly, O-acylTEMPOs allow various transformations and this review encompasses seven topics: (1) Reactivity of O-acylTEMPOs towards n

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38

Srimani, Dipankar, Arup Mukherjee, Alexander F. G. Goldberg, et al. "Cobalt-Catalyzed Hydrogenation of Esters to Alcohols: Unexpected Reactivity Trend Indicates Ester Enolate Intermediacy." Angewandte Chemie 127, no. 42 (2015): 12534–37. http://dx.doi.org/10.1002/ange.201502418.

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39

Douglas, James, Gwydion Churchill, and Andrew D. Smith. "ChemInform Abstract: NHCs in Asymmetric Organocatalysis: Recent Advances in Azolium Enolate Generation and Reactivity." ChemInform 43, no. 41 (2012): no. http://dx.doi.org/10.1002/chin.201241234.

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40

Srimani, Dipankar, Arup Mukherjee, Alexander F. G. Goldberg, et al. "Cobalt-Catalyzed Hydrogenation of Esters to Alcohols: Unexpected Reactivity Trend Indicates Ester Enolate Intermediacy." Angewandte Chemie International Edition 54, no. 42 (2015): 12357–60. http://dx.doi.org/10.1002/anie.201502418.

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41

Hamed, R. B., E. T. Batchelar, I. J. Clifton, and C. J. Schofield. "Mechanisms and structures of crotonase superfamily enzymes – How nature controls enolate and oxyanion reactivity." Cellular and Molecular Life Sciences 65, no. 16 (2008): 2507–27. http://dx.doi.org/10.1007/s00018-008-8082-6.

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42

Wang, Shao-wu, Hui-min Qian, Wei Yao, et al. "Synthesis of rare earth metal complexes incorporating amido and enolate mixed ligands: Characterization and reactivity." Polyhedron 27, no. 13 (2008): 2757–64. http://dx.doi.org/10.1016/j.poly.2008.05.030.

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43

Mendez, Francisco, and Jose L. Gazquez. "Chemical Reactivity of Enolate Ions: The Local Hard and Soft Acids and Bases Principle Viewpoint." Journal of the American Chemical Society 116, no. 20 (1994): 9298–301. http://dx.doi.org/10.1021/ja00099a055.

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44

Xu, Zhou, Hongyi Chen, Zhixun Wang, Anguo Ying, and Liming Zhang. "One-Pot Synthesis of Benzene-Fused Medium-Ring Ketones: Gold Catalysis-Enabled Enolate Umpolung Reactivity." Journal of the American Chemical Society 138, no. 17 (2016): 5515–18. http://dx.doi.org/10.1021/jacs.6b02533.

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45

Werstiuk, Nick Henry, та Chandra Deo Roy. "Experimental and AM1 calculational studies of the deprotonation of bicyclo[2.2.2]octane-2,5-dione and bicyclo[2.2.2]octane-2,6-dione: a study of homoconjugation, inductive, and steric effects on the rates and diastereoselectivities of α enolization". Canadian Journal of Chemistry 73, № 3 (1995): 460–63. http://dx.doi.org/10.1139/v95-060.

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The kinetics of NaOD-catalyzed H/D exchange (enolization) at C3 α to the carbonyl group of bicyclo[2.2.2]octane-2,5-dione (1) and bicyclo[2.2.2]octane-2,6-dione (2) have been studied in 60:40 (v/v) dioxane–D2O at 25.0 °C. The second-order rate constants for exchange are (9.7 ± 1.5) × 10−1 and (3.4 ± 1.2) × 10−5 L mol−1 s−1 for 1 and 2, respectively. Thus, 1, exchanges 76 times faster than bicyclo[2.2.2]octan-2-one (3) (k = (1.27 ± 0.02) × 10−2 L mol−1 s−1), but the 2,6-dione 2 unexpectedly is much less reactive (2.7 × 10−3) than the monoketone. Unlike the large exo selectivity of 658 observed

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46

Morales, Dolores, M. Elena Navarro Clemente, Julio Pérez, Lucía Riera, Víctor Riera та Daniel Miguel. "Reactivity of [MCl(η3-allyl)(1,10-phenanthroline)(CO)2] (M = Mo, W) Complexes toward Enolate Anions". Organometallics 22, № 20 (2003): 4124–28. http://dx.doi.org/10.1021/om030275y.

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47

Heinisch, Gottfried, Thierry Langer, and Jacques Tonnel. "PyridazinesLXXVIIIOn the reactivity of 4-methoxy-[(4-pyridazinyl)methylidene]aniline in ester enolate-imine condensation reactions." Journal of Heterocyclic Chemistry 33, no. 6 (1996): 1731–35. http://dx.doi.org/10.1002/jhet.5570330631.

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48

Srimani, Dipankar, Arup Mukherjee, Alexander F. G. Goldberg, et al. "ChemInform Abstract: Cobalt-Catalyzed Hydrogenation of Esters to Alcohols: Unexpected Reactivity Trend Indicates Ester Enolate Intermediacy." ChemInform 47, no. 7 (2016): no. http://dx.doi.org/10.1002/chin.201607079.

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49

Braunstein, Pierre, Yves Chauvin, Jens Nähring, André DeCian та Jean Fischer. "Synthesis, crystal structures and reactivity of rhodium(III) complexes containing β-ketophosphine and phosphino enolate ligands". J. Chem. Soc., Dalton Trans., № 5 (1995): 863–73. http://dx.doi.org/10.1039/dt9950000863.

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50

Giacobbe, Simone A., and Tino Rossi. "Alkyl groups on the metal enhance the reactivity of the “classical” zirconium enolate of 1-methoxycyclohexanone." Tetrahedron: Asymmetry 7, no. 11 (1996): 3079–82. http://dx.doi.org/10.1016/0957-4166(96)00402-8.

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