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Journal articles on the topic 'Horner–Wadsworth–Emmons procedure'

Author: Grafiati

Published: 4 June 2021

Last updated: 3 February 2022

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1

Abrunhosa-Thomas, Isabelle, Aurélie Plas, Nishanth Kandepedu, Pierre Chalard та Yves Troin. "Efficient synthesis of β’-amino-α,β-unsaturated ketones". Beilstein Journal of Organic Chemistry 9 (6 березня 2013): 486–95. http://dx.doi.org/10.3762/bjoc.9.52.

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A general and simple procedure to access chiral β'-amino-α,β-enones, in seven steps, from an α,β unsaturated ester has been described. The use of a Horner–Wadsworth–Emmons reaction as a key step for generating the β'-amino-α,β-enones, permits access to a range of substrates under mild conditions and in moderate to high yield.

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2

Sano, Shigeki, Tomoya Matsumoto, Munehisa Toguchi, and Michiyasu Nakao. "Facile Two-Step Synthesis of Methyl Bis(2,2,2-trifluoroethyl)phosphonoacetate by Exploiting Garegg–Samuelsson Reaction Conditions." Synlett 29, no. 11 (2018): 1461–64. http://dx.doi.org/10.1055/s-0036-1591566.

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A facile two-step synthesis of methyl bis(2,2,2-trifluoroethyl)phosphonoacetate (Still–Gennari reagent) has been developed by exploiting Garegg–Samuelsson reaction conditions. Starting from trimethyl phosphonoacetate, Still–Gennari reagent was prepared in 94% yield via methyl 2-{bis[(trimethylsilyl)oxy]phosphoryl}acetate intermediate. This synthetic procedure was also used to prepare some kinds of Horner–Wadsworth–Emmons reagents and related compounds.

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3

Bonadies, Francesco, Antonella Cardilli, Alessandra Lattanzi, Liliana R. Orelli, and Arrigo Scettri. "A new procedure for Horner-Wadsworth-Emmons olefination of carbonyl compounds." Tetrahedron Letters 35, no. 20 (1994): 3383–86. http://dx.doi.org/10.1016/s0040-4039(00)76914-0.

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4

BONADIES, F., A. CARDILLI, A. LATTANZI, L. R. ORELLI, and A. SCETTRI. "ChemInform Abstract: A New Procedure for Horner-Wadsworth-Emmons Olefination of Carbonyl Compounds." ChemInform 25, no. 38 (2010): no. http://dx.doi.org/10.1002/chin.199438090.

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5

Matziari, Magdalini, та Yixin Xie. "One-Pot Synthesis of α-Substituted Acrylates". SynOpen 02, № 02 (2018): 0161–67. http://dx.doi.org/10.1055/s-0037-1610357.

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A simple and efficient synthetic method towards α-substituted acrylic esters has been developed using the Horner–Wadsworth–Emmons (HWE) reaction with HCHO after alkylation of phosphonoacetates in a one-pot reaction. This method allows the smooth introduction of various side-chains, such as natural amino acids and other biologically relevant substituents. The use of mild conditions, inexpensive reagents, short reaction times and simple work-up and purification steps provides an effective and general alternative to cumbersome multistep and low-yielding procedures described to date.

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6

Walker, Brian, Paul A. Darkins, M. Anthony McKervey, Hazel M. Moncrieff, and John F. Lynas. "Potent new leucine aminopeptidase inhibitor of novel structure synthesised by a modified Wadsworth–Emmons (Horner) Wittig procedure." Bioorganic & Medicinal Chemistry Letters 10, no. 13 (2000): 1481–82. http://dx.doi.org/10.1016/s0960-894x(00)00261-4.

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7

Lattanzi, Alessandra, Liliana R. Orelli, Patrizia Barone, Antonio Massa, Patrizia Iannece та Arrigo Scettri. "Convenient procedure of Horner–Wadsworth–Emmons olefination for the synthesis of simple and functionalized α,β-unsaturated nitriles". Tetrahedron Letters 44, № 7 (2003): 1333–37. http://dx.doi.org/10.1016/s0040-4039(02)02880-0.

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8

Walker, Brian, Paul A. Darkins, M. Anthony McKervey, Hazel M. Moncrieff, and John F. Lynas. "ChemInform Abstract: Potent New Leucine Aminopeptidase Inhibitor of Novel Structure Synthesized by a Modified Wadsworth-Emmons (Horner) Wittig Procedure." ChemInform 31, no. 42 (2000): no. http://dx.doi.org/10.1002/chin.200042179.

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9

Lubkoll, Jana, Alessia Millemaggi, Alexis Perry, and Richard J. K. Taylor. "Tandem Horner–Wadsworth–Emmons/Heck procedures for the preparation of 3-alkenyl-oxindoles: the synthesis of Semaxanib and GW441756." Tetrahedron 66, no. 33 (2010): 6606–12. http://dx.doi.org/10.1016/j.tet.2010.03.018.

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10

Rossi, Daniela, Anna Carnevale Baraglia, Massimo Serra, Ornella Azzolina, and Simona Collina. "An Efficient Procedure Based on a MW-Assisted Horner–Wadsworth-Emmons Reaction for the Synthesis of (Z)-3,3-Trisubstituted-a,b-unsaturated Esters." Molecules 15, no. 9 (2010): 5928–42. http://dx.doi.org/10.3390/molecules15095928.

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11

Shing, Tony K. M., and Mahmoud Aloui. "Enantiospecific synthesis of (6R, 7S)-diastereoisomer of asperlin." Canadian Journal of Chemistry 68, no. 7 (1990): 1035–37. http://dx.doi.org/10.1139/v90-161.

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An unambiguous synthesis of the (6R,7S)-diastereoisomer of asperlin from D-glucose involving a tandem epoxide formation/intramolecular Wadsworth–Emmons–Horner olefination has established the absolute configuration of the oxirane moiety in natural asperlin as (6S,7R). Keywords: asperlin, synthesis; Wadsworth–Emmons–Horner olefination; epoxide formation.

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12

Ando, Kaori. "Z-Selective Horner-Wadsworth-Emmons Reaction." Journal of Synthetic Organic Chemistry, Japan 58, no. 9 (2000): 869–76. http://dx.doi.org/10.5059/yukigoseikyokaishi.58.869.

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13

Steinbach, Tobias, Christian Wahlen, and Frederik R. Wurm. "Poly(phosphonate)-mediated Horner–Wadsworth–Emmons reactions." Polymer Chemistry 6, no. 7 (2015): 1192–202. http://dx.doi.org/10.1039/c4py01365d.

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Poly(phosphonate)s were used in Horner–Wadsworth–Emmons (HWE) reactions with aldehydes. The progress of the reaction was monitored via in situ-NMR spectroscopy. Minimal purification efforts by precipitation of the polymer are achieved.

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14

Han, Li-Chen, Paul A. Stanley, Paul J. Wood, et al. "Horner–Wadsworth–Emmons approach to piperlongumine analogues with potent anti-cancer activity." Organic & Biomolecular Chemistry 14, no. 31 (2016): 7585–93. http://dx.doi.org/10.1039/c6ob01160h.

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15

Monçalves, Matias, Gabriel M. Zanotto, Josene M. Toldo та ін. "Dipolar vinyl sulfur fluorescent dyes. Synthesis and photophysics of sulfide, sulfoxide and sulfone based D–π–A compounds". RSC Advances 7, № 15 (2017): 8832–42. http://dx.doi.org/10.1039/c6ra27989a.

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16

A. Bisceglia, Juan, and Liliana R. Orelli. "Recent Progress in the Horner-Wadsworth-Emmons Reaction." Current Organic Chemistry 19, no. 9 (2015): 744–75. http://dx.doi.org/10.2174/1385272819666150311231006.

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17

Moradei, Oscar M., Cecile M. du Mortier, and Alicia Fernández Cirelli. "Anomalous Horner-Wadsworth-Emmons reactions on 3,4-enuloses." Tetrahedron 53, no. 22 (1997): 7397–402. http://dx.doi.org/10.1016/s0040-4020(97)00425-0.

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18

Ando, Kaori, and Kyohei Yamada. "Solvent-free Horner–Wadsworth–Emmons reaction using DBU." Tetrahedron Letters 51, no. 25 (2010): 3297–99. http://dx.doi.org/10.1016/j.tetlet.2010.04.072.

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19

Nagaoka, Yasuo, Hideki Inoue, and Kiyoshi Tomioka. "Allenes through Horner-Wadsworth-Emmons Olefination of Alkenylphosphonates." Phosphorus, Sulfur, and Silicon and the Related Elements 177, no. 6-7 (2002): 1843–46. http://dx.doi.org/10.1080/10426500212268.

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20

Ando, Kaori. "ChemInform Abstract: Z-Selective Horner-Wadsworth-Emmons Reaction." ChemInform 32, no. 16 (2001): no. http://dx.doi.org/10.1002/chin.200116288.

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21

Molnár, Katalin, László Takács, Mihály Kádár, Ferenc Faigl, and Zsuzsanna Kardos. "Z- and E-selective Horner–Wadsworth–Emmons reactions." Synthetic Communications 47, no. 13 (2017): 1214–24. http://dx.doi.org/10.1080/00397911.2017.1319487.

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22

Kotkar, S., V. Chavan та A. Sudalai. "Asymmetric Sequential α-Amination-Horner-Wadsworth-Emmons Olefination". Synfacts 2007, № 5 (2007): 0541. http://dx.doi.org/10.1055/s-2007-968407.

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23

Choi, Ji Hye, and Hwan Jung Lim. "Mild one-pot Horner–Wadsworth–Emmons olefination and intramolecular N-arylation for the syntheses of indoles, all regio-isomeric azaindoles, and thienopyrroles." Organic & Biomolecular Chemistry 13, no. 18 (2015): 5131–38. http://dx.doi.org/10.1039/c5ob00528k.

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24

Suzuki, Hideyuki, та Chiaki Kuroda. "(E)-Selective Synthesis of γ-Substituted-β-(Ethoxycarbonyl)Allylsilanes Utilising Ethyl 2-Diphenylphosphono-3-(Trimethylsilyl)Propionate. Improved Synthesis of 11 Membered Carbocycle by a Homo-Cope Reaction". Journal of Chemical Research 2003, № 5 (2003): 310–12. http://dx.doi.org/10.3184/030823403103173930.

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25

Pięta, Marlena, Jacek Kędzia, Anna Janecka, et al. "Novel synthesis and cytotoxic activity of 1,4-disubstituted 3-methylidene-3,4-dihydroquinolin-2(1H)-ones." RSC Advances 5, no. 95 (2015): 78324–35. http://dx.doi.org/10.1039/c5ra16673j.

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26

Liu, Shen, Wenteng Chen, Jing Luo, and Yongping Yu. "[3+3] annulation of allylic phosphoryl-stabilized carbanions/phosphorus ylides and vinyl azides: a practice strategy for synthesis of polyfunctionalized anilines." Chem. Commun. 50, no. 62 (2014): 8539–42. http://dx.doi.org/10.1039/c4cc03462g.

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Tandem Michael addition and Witting or Horner–Wadsworth–Emmons olefination initiated [3+3] annulation between vinyl azides and allylic phosphorus ylides or allylic phosphoryl-stabilized carbanions has been developed.

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27

Mark Heron, B. "Heterocycles from Intramolecular Wittig, Horner and Wadsworth-Emmons Reactions." HETEROCYCLES 41, no. 10 (1995): 2357. http://dx.doi.org/10.3987/rev-95-474.

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28

Peters, Jens-Uwe, Tony Capuano, Silja Weber, Stéphane Kritter, and Matthias Sägesser. "A facile Horner–Wadsworth–Emmons route to 2-quinolones." Tetrahedron Letters 49, no. 25 (2008): 4029–32. http://dx.doi.org/10.1016/j.tetlet.2008.04.088.

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29

Inoue, Hideki, Hiroshi Tsubouchi, Yasuo Nagaoka, and Kiyoshi Tomioka. "Synthesis of allenes by double Horner–Wadsworth–Emmons reaction." Tetrahedron 58, no. 1 (2002): 83–90. http://dx.doi.org/10.1016/s0040-4020(01)01089-4.

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30

Denmark, Scott E., and Isaac Rivera. "Asymmetric Carboalkoxyalkylidenation with a Chiral Horner-Wadsworth-Emmons Reagent." Journal of Organic Chemistry 59, no. 23 (1994): 6887–89. http://dx.doi.org/10.1021/jo00102a005.

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31

Arndtsen, B., M. Morin, and D. St-Cyr. "Horner-Wadsworth-Emmons Reagent as 1,3-Dipolar Cycloaddition Precursor." Synfacts 2011, no. 01 (2010): 0022. http://dx.doi.org/10.1055/s-0030-1259199.

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32

Pipelier, Muriel, Mikhail S. Ermolenko, Angela Zampella, Alain Olesker, and Gabor Lukacs. "Intramolecular Horner-Wadsworth-Emmons Olefination Route to Annulated Carbohydrates." Synlett 1996, no. 01 (1996): 24–26. http://dx.doi.org/10.1055/s-1996-5311.

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33

Kumar, Pradeep, Menaka Pandey, Priti Gupta, and Dilip D. Dhavale. "Retracted Article: Organocatalytic stereoselective synthesis of passifloricin A." Organic & Biomolecular Chemistry 10, no. 9 (2012): 1820–25. http://dx.doi.org/10.1039/c2ob06711k.

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An efficient enantioselective synthesis of passifloricin A has been achieved in high diastereomeric excess by a combination of iterative proline-catalyzed sequential α-aminoxylation, Horner–Wadsworth–Emmons olefination and ring-closing metathesis.

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34

Wang, Yongguang, Ruiyang Bao, Shengdian Huang, and Yefeng Tang. "Bioinspired total synthesis of katsumadain A by organocatalytic enantioselective 1,4-conjugate addition." Beilstein Journal of Organic Chemistry 9 (August 6, 2013): 1601–6. http://dx.doi.org/10.3762/bjoc.9.182.

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Katsumadain A, a naturally occurring inﬂuenza virus neuraminidase (NA) inhibitor, was synthesized by using a bioinspired, organocatalytic enantioselective 1,4-conjugate addition of styryl-2-pyranone with cinnamaldehyde, followed by a tandem Horner–Wadsworth–Emmons/oxa Michael addition.

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35

Vaz, Belén, Noelia Fontán, Marta Castiñeira, Rosana Álvarez, and Ángel R. de Lera. "Synthesis of labile all-trans-7,8,7′,8′-bis-acetylenic carotenoids by bi-directional Horner–Wadsworth–Emmons condensation." Organic & Biomolecular Chemistry 13, no. 10 (2015): 3024–31. http://dx.doi.org/10.1039/c4ob02144d.

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Two symmetrical C<sub>7</sub>,C<sub>8</sub>-acetylenic carotenoids have been stereoselectively prepared using a bi-directional Horner–Wadsworth–Emmons condensation of the C<sub>10</sub>-dialdehyde and C<sub>15</sub>-phosphonates.

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36

Pakhare, Deepali, and Radhika Kusurkar. "Application of Horner–Wadsworth–Emmons olefination for the synthesis of granulatamide A, its E isomer and other amides of tryptamine." New Journal of Chemistry 40, no. 6 (2016): 5428–31. http://dx.doi.org/10.1039/c5nj03533c.

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Horner–Wadsworth–Emmons (HWE) Z-selective olefination was used for the first synthesis of a naturally occurring cytotoxic tryptamine derivative, granulatamide A. The E-isomer of granulatamide A and two other tryptamine derived amides were synthesized by E-selective HWE olefination.

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37

Isbera, Mostafa, Balázs Bognár, József Jekő, Cecilia Sár, Kálmán Hideg, and Tamás Kálai. "Syntheses and Reactions of Pyrroline, Piperidine Nitroxide Phosphonates." Molecules 25, no. 10 (2020): 2430. http://dx.doi.org/10.3390/molecules25102430.

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Organophosphorus compounds occupy a significant position among the plethora of organic compounds, but a limited number of paramagnetic phosphorus compounds have been reported, including paramagnetic phosphonates. This paper describes the syntheses and further transformations of pyrroline and piperidine nitroxide phosphonates by well-established methods, such as the Pudovik, Arbuzov and Horner-Wadsworth-Emmons (HWE) reactions. The reaction of paramagnetic α-bromoketone produced a vinylphosphonate in the Perkow reaction. Paramagnetic α-hydroxyphosphonates could be subjected to oxidation, elimina

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38

Mai, Juri, and Sascha Ott. "The Fascinating World of Phosphanylphosphonates: From Acetylenic Phosphaalkenes to Reductive Aldehyde Couplings." Synlett 30, no. 16 (2019): 1867–85. http://dx.doi.org/10.1055/s-0039-1690129.

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This account highlights the versatility of phosphanylphosphonates, which can be used for the preparation of phosphorus-containing π-systems and as reagents for the reductive coupling of carbonyl compounds to alkenes. Phosphanylphosphonates with metal fragments coordinated to the P-lone pair have been known for a long time and they have been used for the synthesis of phosphaalkenes by means of the phospha-Horner–Wadsworth–Emmons reaction. With the original aim of incorporating phosphorus heteroatoms into classical all-carbon ethynylethene scaffolds, we entered the field of phosphanylphosphonate

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39

Bressin, Robert K., Julia L. Driscoll, Yanping Wang, and Kazunori Koide. "Scalable Preparation of Methylated Ando-Type Horner–Wadsworth–Emmons Reagent." Organic Process Research & Development 23, no. 2 (2019): 274–77. http://dx.doi.org/10.1021/acs.oprd.8b00423.

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40

Tanaka, Kiyoshi, Kenji Otsubo, and Kaoru Fuji. "Enantioselective preparation of allenecarboxylates by asymmetric horner-wadsworth-emmons reaction." Tetrahedron Letters 37, no. 21 (1996): 3735–38. http://dx.doi.org/10.1016/0040-4039(96)00672-7.

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41

Page, Zachariah A., Yao Liu, Egle Puodziukynaite, Thomas P. Russell, and Todd Emrick. "Hydrophilic Conjugated Polymers Prepared by Aqueous Horner–Wadsworth–Emmons Coupling." Macromolecules 49, no. 7 (2016): 2526–32. http://dx.doi.org/10.1021/acs.macromol.5b02501.

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42

Brandt, Peter, Per-Ola Norrby, Ivar Martin, and Tobias Rein. "A Quantum Chemical Exploration of the Horner−Wadsworth−Emmons Reaction." Journal of Organic Chemistry 63, no. 4 (1998): 1280–89. http://dx.doi.org/10.1021/jo971973t.

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43

Kann, Nina, and Tobias Rein. "Asymmetric Horner-Wadsworth-Emmons reactions using meso dialdehydes as substrates." Journal of Organic Chemistry 58, no. 15 (1993): 3802–4. http://dx.doi.org/10.1021/jo00067a010.

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44

Boulos, L. S., and M. H. N. Arsanious. "The Reaction of Wadsworth-Emmons-Horner Reagents witho- andp-Quinoneimines." Phosphorus, Sulfur, and Silicon and the Related Elements 89, no. 1-4 (1994): 185–91. http://dx.doi.org/10.1080/10426509408020448.

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45

Bisceglia, Juan A., and Liliana R. Orelli. "ChemInform Abstract: Recent Progress in the Horner-Wadsworth-Emmons Reaction." ChemInform 46, no. 37 (2015): no. http://dx.doi.org/10.1002/chin.201537252.

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46

MORADEI, O. M., C. M. DU MORTIER, and A. FERNANDEZ-CIRELLI. "ChemInform Abstract: Anomalous Horner-Wadsworth-Emmons Reactions on 3,4-Enuloses." ChemInform 28, no. 40 (2010): no. http://dx.doi.org/10.1002/chin.199740252.

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47

Has-Becker, Senay, Kerstin Bodmann, Reinhard Kreuder, Gabriella Santoni, Tobias Rein, and Oliver Reiser. "High-Pressure Induced Domino-Horner-Wadsworth-Emmons (HWE) - Michael Reactions." Synlett 2001, no. 09 (2001): 1395–98. http://dx.doi.org/10.1055/s-2001-16786.

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48

KUMAMOTO, Takuya, and Kenji KOGA. "Enantioselective Horner-Wadsworth-Emmons Reaction Using Chiral Lithium 2-Aminoalkoxides." CHEMICAL & PHARMACEUTICAL BULLETIN 45, no. 4 (1997): 753–55. http://dx.doi.org/10.1248/cpb.45.753.

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49

Fairlamb, Ian, Amanda Jarvis, and Elizabeth Wells. "Horner-Wadsworth-Emmons Reactions in THF: Effect of Hydroperoxide Species." Synlett 24, no. 12 (2013): 1493–96. http://dx.doi.org/10.1055/s-0033-1339200.

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50

Reddy, Chada Raji, Kamalkishor Warudikar, and Bellamkonda Latha. "Facile Strategy to Access the Indolo[2,3-a]quinolizidine Framework: Synthetic Study on Tangutorine." Synthesis 51, no. 19 (2019): 3715–22. http://dx.doi.org/10.1055/s-0039-1690004.

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An asymmetric synthetic approach to indolo[2,3-a]quinolizidine framework has been developed involving Horner–Wadsworth–Emmons olefination and reductive amination as the key steps. Further, the developed strategy was explored towards the synthesis of tangutorine using Evans aldol reaction for the preparation of desired aldehyde.

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