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Journal articles on the topic 'Reformatsky's reaction'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Cozzi, Pier Giorgio, Alessandro Mignogna, and Luca Zoli. "Catalytic enantioselective Reformatsky reactions." Pure and Applied Chemistry 80, no. 5 (2008): 891–901. http://dx.doi.org/10.1351/pac200880050891.

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The Reformatsky reaction is a venerable named reaction that was introduced more than 120 years ago. Diastereoselective variants based on the use of chiral auxiliary and enantioselective protocols, based on the employment of stoichiometric amount of chiral ligands, have been successfully applied in organic synthesis during the years. However, a facile and general catalytic enantioselective variant was still a difficult task. Recently, we have established a new general and straightforward methodology for catalytic enantioselective Reformatsky reaction based on different concepts. In this paper,

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2

Cozzi, Pier Giorgio, and Eleonora Rivalta. "First enantioselective one-pot, three-component imino Reformatsky reaction." Pure and Applied Chemistry 78, no. 2 (2006): 287–91. http://dx.doi.org/10.1351/pac200678020287.

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The Reformatsky reaction is the well-recognized carbon-carbon bond-forming reaction of α-halo esters with aldehydes or ketones in the presence of Zn metal to give β-hydroxy esters. Recently, it has been reported that Rh- and Ni-catalyzed Reformatsky reaction, in which R2Zn (R = Me, Et) acts as the Zn source, reacted smoothly with carbonyl compounds and imines. Taking advantage of N-methylephedrine as a cheap and recoverable chiral ligand, we have discovered the first homogeneous enantioselective Ni-catalyzed imino Reformatsky reaction. The process is a one-pot, three-component reaction, in whi

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3

De Munck, Lode, Verena Sukowski, Carlos Vila, M. Carmen Muñoz, and José R. Pedro. "Catalytic enantioselective aza-Reformatsky reaction with seven-membered cyclic imines dibenzo[b,f][1,4]oxazepines." Organic Chemistry Frontiers 4, no. 8 (2017): 1624–28. http://dx.doi.org/10.1039/c7qo00329c.

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4

Pellissier, Hélène. "Recent developments in the asymmetric Reformatsky-type reaction." Beilstein Journal of Organic Chemistry 14 (February 2, 2018): 325–44. http://dx.doi.org/10.3762/bjoc.14.21.

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This review collects the most important developments in asymmetric Reformatsky-type reactions published since the beginning of 2013, including both diastereoselective methodologies based on the use of chiral substrates and enantioselective catalytic procedures.

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5

Mylari, Banavara L., and William J. Zembrowski. "Reformatsky reaction: carboxymethylenation of cyclic anhydrides and reactions of products thereof." Journal of Organic Chemistry 56, no. 7 (1991): 2587–89. http://dx.doi.org/10.1021/jo00007a061.

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6

Tarui, Atsushi, Takeshi Ikebata, Kazuyuki Sato, Masaaki Omote та Akira Ando. "Enantioselective synthesis of α,α-difluoro-β-lactams using amino alcohol ligands". Org. Biomol. Chem. 12, № 33 (2014): 6484–89. http://dx.doi.org/10.1039/c4ob01184h.

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7

Park, Doo-Han, Ho-Jin Choi, and Sang-Gi Lee. "Enantioselective Reformatsky Reaction Using Cinchona Alkaloids as Chiral Ligands." Journal of the Korean Chemical Society 47, no. 6 (2003): 597–600. http://dx.doi.org/10.5012/jkcs.2003.47.6.597.

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8

Chen, Zhiwei, Hao Chen, Xiaofeng Yang, and Xiangqing Chang. "Novel One-Pot Cyclization of the Blaise Reaction Intermediate and Arylglyoxals: The Synthesis of Substituted NH-Pyrroles." Synlett 28, no. 12 (2017): 1463–66. http://dx.doi.org/10.1055/s-0036-1588168.

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A novel tandem Blaise reaction for the one-pot synthesis of substituted NH-pyrroles was described. The Blaise reaction intermediate, generated in situ from Reformatsky reagent and nitrile, reacted with arylglyoxals chemoselectively to afford a wide variety of substituted NH-pyrroles in good yields.

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9

Chaudhari, Tohasib Yusub, Urvashi Urvashi, Sandeep K. Ginotra, Pooja Yadav, Gulshan Kumar, and Vibha Tandon. "Regioselective synthesis of functionalized dihydroisoquinolines from o-alkynylarylaldimines via the Reformatsky reaction." Organic & Biomolecular Chemistry 14, no. 41 (2016): 9896–906. http://dx.doi.org/10.1039/c6ob01790h.

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10

Sgreccia, Laura, Marco Bandini, Stefano Morganti, Arianna Quintavalla, Achille Umani-Ronchi, and Pier Giorgio Cozzi. "Titanium-catalyzed Reformatsky-type reaction." Journal of Organometallic Chemistry 692, no. 15 (2007): 3191–97. http://dx.doi.org/10.1016/j.jorganchem.2007.02.037.

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11

Wolf, Christian, and Max Moskowitz. "Bisoxazolidine-Catalyzed Enantioselective Reformatsky Reaction." Journal of Organic Chemistry 76, no. 15 (2011): 6372–76. http://dx.doi.org/10.1021/jo200774e.

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12

Cozzi, P. "Catalytic Enantioselective Imino-Reformatsky Reaction." Synfacts 2007, no. 1 (2007): 0050. http://dx.doi.org/10.1055/s-2006-955713.

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13

Furstner, Alois. "ChemInform Abstract: The Reformatsky Reaction." ChemInform 30, no. 27 (2010): no. http://dx.doi.org/10.1002/chin.199927291.

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14

Kanai, Kazuo, Hitoshi Wakabayashi, and Toshio Honda. "Rhodium-Catalyzed Reformatsky-Type Reaction." Organic Letters 2, no. 16 (2000): 2549–51. http://dx.doi.org/10.1021/ol006268c.

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15

Braun, Manfred. "The Asymmetric Difluoro‐Reformatsky Reaction." European Journal of Organic Chemistry 2021, no. 12 (2021): 1825–36. http://dx.doi.org/10.1002/ejoc.202100004.

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16

Mahasneh, Ali S. "Tin(II)chloride Mediated Addition Reaction of Bromonitromethane to Aldehydes." Zeitschrift für Naturforschung B 60, no. 4 (2005): 416–18. http://dx.doi.org/10.1515/znb-2005-0411.

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Bromonitromethane adds to aliphatic aldehydes in the presence of tin(II) chloride to yield β -nitro alcohols via a Reformatsky-type reaction in high yields, while aromatic aldehydes give low yields. The products were characterized by IR, NMR, and mass spectroscopy and by elemental analysis

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17

Fang, Chao, Yan Yin, Heng Zhang та Fan Hong Wu. "Enantioselective Reformatsky Reaction between Cinnamaldehyde and Diflurinated Organozinc Reagent: Synthesis of Chiral γ,γ-difluoro-β-hydroxy Esters as Precursors of Statin Analogues". Advanced Materials Research 881-883 (січень 2014): 154–58. http://dx.doi.org/10.4028/www.scientific.net/amr.881-883.154.

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Reaction conditions of asymmetric Reformatsky reaction between cinnamaldehyde 1 and ethyl bromodifluoroacetate 2 were investigated. Finally, (1S, 2R)-N,N-dimethyl-2-aminol-1, 2-diphenylethanol (ligand C) was proved to be the best ligand for this transformation and up to 37% ee was obtained with THF as solvent in -40 degree.

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18

Dutta, Lakshmi Narayan, Manju Bhattacharyya, and Asoke Kumar Sarkar. "A study of the Reformatsky reaction on formylcoumarins." Canadian Journal of Chemistry 73, no. 9 (1995): 1556–62. http://dx.doi.org/10.1139/v95-193.

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The reactions of bromozinc enolate reagents on formylcoumarins (1, 2) afforded spiro-γ-lactones (15–18), furan derivatives (13, 14), and coumarinylcarbinols (3, 4) as highly unusual products along with the expected β-hydroxyesters (5–12). Stereochemical features of some of these products turned out to be highly informative and were unambiguously corroborated. Keywords: formylcoumarins, unusual Reformatsky products, stereochemistry.

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19

Huck, L., M. Berton, A. de la Hoz, A. Díaz-Ortiz, and J. Alcázar. "Reformatsky and Blaise reactions in flow as a tool for drug discovery. One pot diversity oriented synthesis of valuable intermediates and heterocycles." Green Chemistry 19, no. 6 (2017): 1420–24. http://dx.doi.org/10.1039/c6gc02619b.

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20

MYLARI, B. L., and W. J. ZEMBROWSKI. "ChemInform Abstract: Reformatsky Reaction: Carboxymethylenation of Cyclic Anhydrides and Reactions of Products Thereof." ChemInform 22, no. 37 (2010): no. http://dx.doi.org/10.1002/chin.199137146.

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21

Luo, Ren Shi, Lu Ouyang, Jian Hua Liao та Yan Ping Xia. "Access to β-Hydroxyl Esters via Copper-Catalyzed Reformatsky Reaction of Ketones and Aldehydes". Synlett 31, № 14 (2020): 1418–22. http://dx.doi.org/10.1055/s-0040-1707110.

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An efficient and simple Cu-catalyzed Reformatsky reaction of ketones and aldehydes has been accomplished with ethyl iodoacetate. Excellent yields of β-hydroxyl esters were achieved with a range of ketones and aldehydes, which varied from aromatic to aliphatic, unsaturated to saturated ketones and aldehydes. This practical and convenient transformation was conducted with inexpensive, readily available, and commercial starting materials under mild reaction conditions.

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22

Fürstner, Alois. "Recent Advancements in the Reformatsky Reaction." Synthesis 1989, no. 08 (1989): 571–90. http://dx.doi.org/10.1055/s-1989-27326.

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23

Maestro, Aitor, Edorta Martinez de Marigorta, Francisco Palacios, and Javier Vicario. "Enantioselective Aza-Reformatsky Reaction with Ketimines." Organic Letters 21, no. 23 (2019): 9473–77. http://dx.doi.org/10.1021/acs.orglett.9b03669.

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24

Baba, A., S. Babu, M. Yasuda, Y. Okabe, and I. Shibata. "Stereoselective Reformatsky Reaction of Indium Enolates." Synfacts 2006, no. 9 (2006): 0930. http://dx.doi.org/10.1055/s-2006-949268.

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25

Bortolussi, Michel, and Jacqueline Seyden-penne. "Reformatsky Reaction Using Zn/Ag Couple." Synthetic Communications 19, no. 13-14 (1989): 2355–61. http://dx.doi.org/10.1080/00397918908052634.

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26

Cozzi, P. "Mn-Catalyzed Reformatsky Reaction with Ketones." Synfacts 2006, no. 7 (2006): 0698. http://dx.doi.org/10.1055/s-2006-941862.

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27

Shibata, Ikuya, Takashi Yamaguchi, Akio Baba, and Haruo Matsuda. "Reformatsky Type Reaction Promoted by Hexabutyldistannane." Chemistry Letters 22, no. 1 (1993): 97–100. http://dx.doi.org/10.1246/cl.1993.97.

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28

Fernández-Ibáñez, M. Ángeles, Beatriz Maciá, Adriaan J. Minnaard, and Ben L. Feringa. "Catalytic enantioselective Reformatsky reaction with ketones." Chemical Communications, no. 22 (2008): 2571. http://dx.doi.org/10.1039/b801749b.

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29

Cao, Qun, Roderick T. Stark, Ian A. Fallis, and Duncan L. Browne. "A Ball‐Milling‐Enabled Reformatsky Reaction." ChemSusChem 12, no. 12 (2019): 2554–57. http://dx.doi.org/10.1002/cssc.201900886.

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30

Cozzi, Pier Giorgio. "A Catalytic Enantioselective Imino-Reformatsky Reaction." Advanced Synthesis & Catalysis 348, no. 15 (2006): 2075–79. http://dx.doi.org/10.1002/adsc.200606178.

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31

Fernández-Ibáñez, M. Ángeles, Beatriz Maciá, Adriaan J Minnaard, and Ben L Feringa. "Catalytic Enantioselective Reformatsky Reaction with Aldehydes." Angewandte Chemie International Edition 47, no. 7 (2008): 1317–19. http://dx.doi.org/10.1002/anie.200704841.

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32

Braun, Manfred, Anja Vonderhagen, and Delia Waldmüller. "Enantioselective reformatsky reaction of methyl bromodifluoroacetate." Liebigs Annalen 1995, no. 8 (1995): 1447–50. http://dx.doi.org/10.1002/jlac.1995199508196.

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33

Feringa, B., M. Fernández-Ibáñez, B. Maciá, and A. Minnaard. "Asymmetric Reformatsky Reaction withortho-Substituted Diarylketones." Synfacts 2008, no. 11 (2008): 1196. http://dx.doi.org/10.1055/s-0028-1083436.

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34

Orsini, F., and G. Sello. "Transition Metals-Mediated Reformatsky Reactions." Current Organic Synthesis 1, no. 2 (2004): 111–35. http://dx.doi.org/10.2174/1570179043485385.

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35

Durandetti, Muriel, and Jacques Périchon. "Iron-Catalysed Reformatsky-Type Reactions." Synthesis 2006, no. 9 (2006): 1542–48. http://dx.doi.org/10.1055/s-2006-926432.

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36

Isoda, Motoyuki, Kazuyuki Sato, Yurika Kunugi, et al. "Rh-Catalyzed reductive Mannich-type reaction and its application towards the synthesis of (±)-ezetimibe." Beilstein Journal of Organic Chemistry 12 (July 27, 2016): 1608–15. http://dx.doi.org/10.3762/bjoc.12.157.

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An effective synthesis for syn-β-lactams was achieved using a Rh-catalyzed reductive Mannich-type reaction. A rhodium–hydride complex (Rh–H) derived from diethylzinc (Et2Zn) and a Rh catalyst was used for the 1,4-reduction of an α,β-unsaturated ester to give a Reformatsky-type reagent, which in turn, reacted with an imine to give the syn-β-lactam. Additionally, the reaction was applied to the synthesis of (±)-ezetimibe, a potent β-lactamic cholesterol absorption inhibitor.

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37

Lin, Ning, Miao-Miao Chen, Ren-Shi Luo, Yan-Qiu Deng, and Gui Lu. "Indolinylmethanol catalyzed enantioselective Reformatsky reaction with ketones." Tetrahedron: Asymmetry 21, no. 23 (2010): 2816–24. http://dx.doi.org/10.1016/j.tetasy.2010.11.004.

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38

Ribeiro, Carlos, and Florence de Farias. "Chiral Ligands in the Asymmetric Reformatsky Reaction." Mini-Reviews in Organic Chemistry 3, no. 1 (2006): 1–10. http://dx.doi.org/10.2174/157019306775474176.

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39

Kanai, Kazuo, Hitoshi Wakabayashi, and Toshio Honda. "ChemInform Abstract: Rhodium-Catalyzed Reformatsky-Type Reaction." ChemInform 31, no. 46 (2010): no. http://dx.doi.org/10.1002/chin.200046044.

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40

Wolf, Christian, and Max Moskowitz. "ChemInform Abstract: Bisoxazolidine-Catalyzed Enantioselective Reformatsky Reaction." ChemInform 42, no. 48 (2011): no. http://dx.doi.org/10.1002/chin.201148071.

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41

Fernández-Ibáñez, M. Ángeles, Beatriz Maciá, Adriaan J. Minnaard, and Ben L. Feringa. "Catalytic Enantioselective Reformatsky Reaction withortho-Substituted Diarylketones." Organic Letters 10, no. 18 (2008): 4041–44. http://dx.doi.org/10.1021/ol801574m.

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42

Chandrasekharam, M., Laxminaraya Bhat, Hiriyakkanavar Ila, and Hiriyakkanavar Junjappa. "Reformatsky reaction on thiocarbonyl compounds: New CC bond forming reaction." Tetrahedron Letters 34, no. 40 (1993): 6439–42. http://dx.doi.org/10.1016/0040-4039(93)85065-5.

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43

Cozzi, Pier Giorgio. "Reformatsky Reactions Meet Catalysis and Stereoselectivity." Angewandte Chemie International Edition 46, no. 15 (2007): 2568–71. http://dx.doi.org/10.1002/anie.200604344.

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44

Cozzi, Pier Giorgio. "Reformatsky Reactions Meet Catalysis and Stereoselectivity." Angewandte Chemie International Edition 46, no. 37 (2007): 6948. http://dx.doi.org/10.1002/anie.200790187.

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45

Ross, Nathan A., and Richard A. Bartsch. "High-Intensity Ultrasound-Promoted Reformatsky Reactions." Journal of Organic Chemistry 68, no. 2 (2003): 360–66. http://dx.doi.org/10.1021/jo0261395.

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46

Fontenelle, Clément Q., Matthew Conroy, Mark Light, Thomas Poisson, Xavier Pannecoucke та Bruno Linclau. "Stereoselectivity of the Honda–Reformatsky Reaction in Reactions with Ethyl Bromodifluoroacetate with α-Oxygenated Sulfinylimines". Journal of Organic Chemistry 79, № 9 (2014): 4186–95. http://dx.doi.org/10.1021/jo500396p.

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47

Benfatti, Fides, and Pier Giorgio Cozzi. "Copper-promoted enantioselective Reformatsky-type reaction with ketones." Tetrahedron: Asymmetry 21, no. 11-12 (2010): 1503–6. http://dx.doi.org/10.1016/j.tetasy.2010.04.058.

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48

Ocampo, Rogelio, and William R. Dolbier. "The Reformatsky reaction in organic synthesis. Recent advances." Tetrahedron 60, no. 42 (2004): 9325–74. http://dx.doi.org/10.1016/j.tet.2004.07.018.

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49

Knochel, P., R. Kloetzing, and T. Thaler. "Asymmetric Reformatsky Reaction with an Isoborneol Derivative Ligand." Synfacts 2006, no. 5 (2006): 0475. http://dx.doi.org/10.1055/s-2006-934354.

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50

Ishihara, T., T. Shimada, M. Yoshioka, and T. Konno. "Asymmetric Reformatsky Reaction with a Chiral Oxazolidinone Auxiliary." Synfacts 2006, no. 5 (2006): 0464. http://dx.doi.org/10.1055/s-2006-934357.

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