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Journal articles on the topic 'Umpolung'

Author: Grafiati

Published: 4 June 2021

Last updated: 7 July 2024

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1

J. Boluda, Carlos, Carolina Juncá, Emily Soto, Darah De la Cruz, and Anny Peña. "Umpolung in reactions catalyzed by thiamine pyrophosphate dependent enzymes." Ciencia, Ambiente y Clima 2, no. 2 (December 13, 2019): 27–42. http://dx.doi.org/10.22206/cac.2019.v2i2.pp27-42.

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El intercambio temporal del carácter electrofílico/nucleofí-lico de un átomo mediante manipulación química, es cono-cido con el vocablo alemán de umpolung. Esta inversión de polaridad permite explorar nuevas posibilidades sintéticas que no pueden llevarse a cabo partiendo de la reactividad normal de los grupos funcionales. Se trata de una herra-mienta sintética útil, que también es utilizada por ciertas enzimas en determinadas reacciones bioquímicas que tienen lugar en las células. Las enzimas dependientes del pirofosfato de tiamina, como la piruvato descarboxilasa, la piruvato deshidrogenasa, la α-cetoglutarato deshidrogenasa, la deshidrogenasa de α-cetoácidos de cadena ramificada y la transcetolasa, proporcionan ejemplos claros de umpolungen reacciones celulares. En esta revisión, tras una discusión sobre el significado del término umpolung encontrado en la literatura química, se analizan los mecanismos de reacción y el significado bioquímico de las transformaciones llevadas a cabo por las enzimas mencionadas.

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2

Sukhorukov, Alexey Yu. "Umpolung of Enamines: An Overview on Strategies and Synthons." Synlett 31, no. 05 (January 13, 2020): 439–49. http://dx.doi.org/10.1055/s-0037-1610741.

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Umpolung strategies are of considerable interest to organic chemists because they provide alternative synthetic routes to those imposed by the natural polarity of classical synthons. Reverse-polarity reactions of aldehydes, α,β-unsaturated carbonyl compounds, and imines are deeply embedded in the methodology of organic synthesis. In recent years, umpolung of enols and enamines has received much attention as a novel strategy to access α-substituted ketones. Here, state-of-the-art approaches to umpolung of enamine reactivity are discussed, with a particular focus on recent developments in this field from the author’s research group.1 Introduction2 Approaches toward Umpolung of Enamines3 Umpolung of Enamines through Single-Electron Oxidation4 Azadienes as Synthetic Equivalents of Enamine Umpolung Synthons5 Enamines Possessing a Leaving Group at the Nitrogen Atom6 Enamines Possessing a Directing Group at the Nitrogen Atom7 Summary and Outlook

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3

Huang, Zhusheng, Qingqing Chen, Xiuqin Yang, Yang Liu, Li Zhang, Tao Lu, and Qingfa Zhou. "Phosphine-mediated domino reactions of phthalimidomalonates with allenoates or but-2-ynoate: facile entry into highly functionalized pyrroloisoindolinone derivatives." Organic Chemistry Frontiers 4, no. 6 (2017): 967–71. http://dx.doi.org/10.1039/c6qo00775a.

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A phosphine-mediated γ-umpolung/Wittig/γ-umpolung reaction between phthalimidomalonates and allenoates/but-2-ynoate furnishes highly functionalized pyrroloisoindolinone derivatives in synthetically useful yields.

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4

Sun, Xi-Shang, Xin Chang, Li-Min Shi, Zuo-Fei Wang, Liang Wei, and Chun-Jiang Wang. "Palladium catalyzed cascade umpolung allylation/acetalation for the construction of quaternary 3-amino oxindoles." Chemical Communications 57, no. 64 (2021): 7958–61. http://dx.doi.org/10.1039/d1cc03075b.

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A highly diastereoselective synthesis of quaternary 3-amino oxindoles via a palladium catalyzed three-component cascade umpolung allylation/acetalation process has been developed. The current method could be extended to cascade umpolung allenylation/acetalation.

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5

Hou, Yading, Yuwen Zhang, and Xiaofeng Tong. "Phosphine-catalysed α-umpolung addition of nucleophiles to δ-acetoxy allenoates: stereoselective synthesis of 2,4-dienoates." Organic & Biomolecular Chemistry 16, no. 29 (2018): 5245–49. http://dx.doi.org/10.1039/c8ob00933c.

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The first example of phosphine-catalyzed α-umpolung addition of nucleophiles to allenoates is described, which features the use of δ-acetoxy allenoate to generate a 3-phosphonium-2,4-dienoate intermediate, thus facilitating the α-umpolung addition of nucleophiles.

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6

Finkbeiner, Peter, and Boris J. Nachtsheim. "Umpolung von Iminen." Nachrichten aus der Chemie 63, no. 11 (November 2015): 1089–93. http://dx.doi.org/10.1002/nadc.201590367.

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7

Allmann, Rudolf, Wolfgang Hanefeld, Magda Krestel, and Bernd Spangenberg. "A Sulfene Umpolung." Angewandte Chemie International Edition in English 26, no. 11 (November 1987): 1133–34. http://dx.doi.org/10.1002/anie.198711331.

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8

Zhao, Baoguo, and Wen-Wen Chen. "Decarboxylative Umpolung Synthesis of Amines from Carbonyl Compounds." Synlett 31, no. 16 (July 12, 2020): 1543–50. http://dx.doi.org/10.1055/s-0040-1707157.

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2-Azaallyl anions are valuable intermediates which have versatile applications in functionalization with various electrophiles. Decarboxylation of the imines formed from aromatic aldehydes and α,α-diphenylglycine provides an interesting and efficient way to generate delocalized 2-azaallyl anions, which display high reactivity toward different electrophiles with excellent regioselectivity at the diphenylketimino aryl carbon of the 2-azaallyl anions. The transformation produces various amines in good yields under very mild conditions. This Synpacts article highlights the recent advances on the decarboxylative umpolung synthesis of amines from carbonyl compounds.1 Introduction2 Decarboxylative Umpolung Reactions of Carbonyl Compounds with Different Electrophiles2.1 Reaction with π-Allyl–Pd(II) Species2.2 Reaction with Morita–Baylis–Hillman Adducts2.3 Reaction with Imines2.3.1 Intermolecular Reaction with N-Ts Imines2.3.2 Intramolecular Reaction with Chiral N-tert-Butanesulfinyl Imines2.4 Reaction with Aldehydes and Ketones3 Decarboxylative Umpolung Reaction of α,β-Unsaturated Aldehydes with Aldehydes4 Conclusion

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9

Jaenicke, Lothar. "Umpolung der Peptid-Synthese." Chemie in unserer Zeit 44, no. 5 (October 2010): 319. http://dx.doi.org/10.1002/ciuz.201090065.

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10

Korte, Monia. "Die Umpolung des Erdmagnetfelds." Physik in unserer Zeit 50, no. 6 (November 2019): 308. http://dx.doi.org/10.1002/piuz.201970613.

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11

Xia, Xiaowen, Bocheng Chen, Xiaojun Zeng, and Bo Xu. "Synthesis of α-amino ketones through aminations of umpoled enolates." Organic & Biomolecular Chemistry 16, no. 38 (2018): 6918–22. http://dx.doi.org/10.1039/c8ob02004c.

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12

Kondo, Yui, Kazunori Nagao, and Hirohisa Ohmiya. "Reductive umpolung for asymmetric synthesis of chiral α-allenic alcohols." Chemical Communications 56, no. 54 (2020): 7471–74. http://dx.doi.org/10.1039/d0cc02619k.

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13

Zhang, Sheng, Wenchao Gao, Jianxue Shi, Jingjing Li, Fengyi Li, Yating Liang, Xuan Zhan, and Man-Bo Li. "Regioselective umpolung addition of dicyanobenzene to α,β-unsaturated alkenes enabled by electrochemical reduction." Organic Chemistry Frontiers 9, no. 5 (2022): 1261–66. http://dx.doi.org/10.1039/d1qo01852c.

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14

Tokumaru, Kazuyuki, and Jeffrey N. Johnston. "A convergent synthesis of 1,3,4-oxadiazoles from acyl hydrazides under semiaqueous conditions." Chemical Science 8, no. 4 (2017): 3187–91. http://dx.doi.org/10.1039/c7sc00195a.

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15

Liu, Feng, Guoqing Zhao, Weiqi Cai, Dongfang Xu, and Baoguo Zhao. "Aminative Umpolung cyclization for synthesis of chiral exocyclic vicinal diamines." Organic & Biomolecular Chemistry 16, no. 40 (2018): 7498–502. http://dx.doi.org/10.1039/c8ob02000k.

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16

Aksenov, Alexander V., Alexander N. Smirnov, Nicolai A. Aksenov, Asiyat S. Bijieva, Inna V. Aksenova, and Michael Rubin. "Benzimidazoles and benzoxazoles via the nucleophilic addition of anilines to nitroalkanes." Organic & Biomolecular Chemistry 13, no. 14 (2015): 4289–95. http://dx.doi.org/10.1039/c5ob00131e.

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17

Lin, Qiqiao, Yuanzhen Li, Deb Kumar Das, Guoxiang Zhang, Zhifei Zhao, Shuang Yang, and Xinqiang Fang. "N-Heterocyclic carbene-catalyzed desymmetrization of functionalized 1,4-dienes via Stetter Reaction." Chemical Communications 52, no. 38 (2016): 6459–62. http://dx.doi.org/10.1039/c6cc01011c.

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18

Tu, Peng-Cheng, Lin Zhou, Alexander M. Kirillov, Ran Fang, and Lizi Yang. "Computational study on the NHC-catalyzed synthesis of 2,3-disubstituted indoles: mechanism, key intermediate and the role of the catalyst." Organic Chemistry Frontiers 5, no. 8 (2018): 1356–65. http://dx.doi.org/10.1039/c8qo00139a.

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19

Donnelly, Joseph, Christoph R. Müller, Lotte Wiermans, Christopher J. Chuck, and Pablo Domínguez de María. "Upgrading biogenic furans: blended C10–C12 platform chemicals via lyase-catalyzed carboligations and formation of novel C12 – choline chloride-based deep-eutectic-solvents." Green Chemistry 17, no. 5 (2015): 2714–18. http://dx.doi.org/10.1039/c5gc00342c.

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20

Pahlavan, Farideh, Sedigheh Saddat Moosavi, Amin Reza Zolghadr, and Nasser Iranpoor. "Electronic origins of the stereochemistry in β-lactam formed through the Staudinger reaction catalyzed by a nucleophile." RSC Advances 13, no. 48 (2023): 33654–67. http://dx.doi.org/10.1039/d3ra05286a.

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21

Shimizu, Makoto, Yuki Furukawa, Isao Mizota, and Yusong Zhu. "An umpolung reaction of α-iminonitriles and its application to the synthesis of aminomalononitriles." New Journal of Chemistry 44, no. 1 (2020): 152–61. http://dx.doi.org/10.1039/c9nj05114g.

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22

Schwieter, Kenneth E., and Jeffrey N. Johnston. "A one-pot amidation of primary nitroalkanes." Chemical Communications 52, no. 1 (2016): 152–55. http://dx.doi.org/10.1039/c5cc08415f.

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23

Tan, Zhuozhen, Xiaolong Wan, Zhenhua Zang, Qun Qian, Wei Deng, and Hegui Gong. "Ni-catalyzed asymmetric reductive allylation of aldehydes with allylic carbonates." Chem. Commun. 50, no. 29 (2014): 3827–30. http://dx.doi.org/10.1039/c3cc49859j.

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24

Yoshida, Yasushi, Mayu Kukita, Kazuki Omori, Takashi Mino, and Masami Sakamoto. "Iminophosphorane-mediated regioselective umpolung alkylation reaction of α-iminoesters." Organic & Biomolecular Chemistry 19, no. 20 (2021): 4551–64. http://dx.doi.org/10.1039/d1ob00596k.

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25

Liu, Feng, Jiaxin Tian, Yong Liu, Chuangan Tao, Hao Zhu, Aina Zhang, Dongfang Xu, and Baoguo Zhao. "Decarboxylative Umpolung of conjugated enals to β-carbanions for intramolecular nucleophilic addition to an aldehyde." Organic Chemistry Frontiers 4, no. 8 (2017): 1586–89. http://dx.doi.org/10.1039/c6qo00846a.

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26

Cheng, Kunpeng, Yishu Bao, Jiahua Wang, Zonghao Dai, Jinrong Lu, and Qingfa Zhou. "Hydroxy-assisted regio- and stereoselective synthesis of functionalized alkenes via phosphine-catalyzed β′-umpolung addition of o-hydroxy aromatic aldimines to allenoates." Organic Chemistry Frontiers 5, no. 15 (2018): 2375–78. http://dx.doi.org/10.1039/c8qo00460a.

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27

Targel, Tom A., Jayprakash N. Kumar, O. Svetlana Shneider, Sukanta Bar, Natalia Fridman, Shimon Maximenko, and Alex M. Szpilman. "Oxidative asymmetric umpolung alkylation of Evans’ β-ketoimides using dialkylzinc nucleophiles." Organic & Biomolecular Chemistry 13, no. 9 (2015): 2546–49. http://dx.doi.org/10.1039/c4ob02601b.

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28

Gruber, Stefan, Simon M. Ametamey, and Roger Schibli. "Unexpected reactivity of cyclic perfluorinated iodanes with electrophiles." Chemical Communications 54, no. 65 (2018): 8999–9002. http://dx.doi.org/10.1039/c8cc04558e.

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29

Ramarao, Jakkula, Sanjay Yadav, Killari Satyam, and Surisetti Suresh. "N-Heterocyclic carbene (NHC)-catalyzed oxidation of unactivated aldimines to amides via imine umpolung under aerobic conditions." RSC Advances 12, no. 13 (2022): 7621–25. http://dx.doi.org/10.1039/d2ra00897a.

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30

Vishe, Mahesh, and Jeffrey N. Johnston. "The inverted ketene synthon: a double umpolung approach to enantioselective β2,3-amino amide synthesis." Chemical Science 10, no. 4 (2019): 1138–43. http://dx.doi.org/10.1039/c8sc04330b.

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31

Giovannini, P. P., O. Bortolini, A. Cavazzini, R. Greco, G. Fantin, and A. Massi. "Expanding the scope of enzymatic carboligation reactions in flow-mode: production of optically active tertiary alcohols with packed-bed micro-bioreactors." Green Chem. 16, no. 8 (2014): 3904–15. http://dx.doi.org/10.1039/c4gc00838c.

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32

Yang, Huan, Li Zhang, Fei-Yu Zhou, and Lei Jiao. "An umpolung approach to the hydroboration of pyridines: a novel and efficient synthesis of N-H 1,4-dihydropyridines." Chemical Science 11, no. 3 (2020): 742–47. http://dx.doi.org/10.1039/c9sc05627k.

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33

Ramachary, Dhevalapally B., T. Prabhakar Reddy, and A. Suresh Kumar. "Organocatalytic umpolung annulative dimerization of ynones for the synthesis of 5-alkylidene-2-cyclopentenones." Organic & Biomolecular Chemistry 15, no. 46 (2017): 9785–89. http://dx.doi.org/10.1039/c7ob02424j.

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34

Yan, Si-Shun, Lei Zhu, Jian-Heng Ye, Zhen Zhang, He Huang, Huiying Zeng, Chao-Jun Li, Yu Lan, and Da-Gang Yu. "Ruthenium-catalyzed umpolung carboxylation of hydrazones with CO2." Chemical Science 9, no. 21 (2018): 4873–78. http://dx.doi.org/10.1039/c8sc01299g.

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35

Lü, Ping, and Yan-Guang WANG. "Umpolung in Fundamental Organic Reactions." University Chemistry 31, no. 5 (2016): 49–59. http://dx.doi.org/10.3866/pku.dxhx201511019.

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36

Zhan, Miao, Xiang Pu, Bin He, Dawen Niu, and Xia Zhang. "Intramolecular Umpolung Allylation of Imines." Organic Letters 20, no. 18 (September 11, 2018): 5857–60. http://dx.doi.org/10.1021/acs.orglett.8b02536.

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37

Gudat, Dietrich, Asadollah Haghverdi, and Martin Nieger. "Umpolung von P-H-Bindungen." Angewandte Chemie 112, no. 17 (September 1, 2000): 3211–14. http://dx.doi.org/10.1002/1521-3757(20000901)112:17<3211::aid-ange3211>3.0.co;2-a.

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38

Gudat, Dietrich, Asadollah Haghverdi, and Martin Nieger. "Umpolung of P−H Bonds." Angewandte Chemie 39, no. 17 (September 1, 2000): 3084–86. http://dx.doi.org/10.1002/1521-3773(20000901)39:17<3084::aid-anie3084>3.0.co;2-r.

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39

Hussain, Yaseen, and Pankaj Chauhan. "Catalytic asymmetric umpolung reactions of imines via 2-azaallyl anion intermediates." Organic & Biomolecular Chemistry 19, no. 19 (2021): 4193–212. http://dx.doi.org/10.1039/d1ob00409c.

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40

Zhang, Kui, Lingchao Cai, Zhongyue Yang, K. N. Houk, and Ohyun Kwon. "Bridged [2.2.1] bicyclic phosphine oxide facilitates catalytic γ-umpolung addition–Wittig olefination." Chemical Science 9, no. 7 (2018): 1867–72. http://dx.doi.org/10.1039/c7sc04381c.

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41

Lu, Xun, and Uwe Schneider. "Aza-Morita–Baylis–Hillman reactions catalyzed by a cyclopropenylidene." Chemical Communications 52, no. 88 (2016): 12980–83. http://dx.doi.org/10.1039/c6cc06201f.

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42

Saito, Rei, Naohiro Uemura, Hiroki Ishikawa, Akina Magara, Yasushi Yoshida, Takashi Mino, Yoshio Kasashima, and Masami Sakamoto. "Umpolung cyclization reaction of N-cinnamoylthioureas in the presence of DBU." Organic & Biomolecular Chemistry 16, no. 42 (2018): 7910–19. http://dx.doi.org/10.1039/c8ob02066c.

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43

Chavannavar, Aditi P., Allen G. Oliver, and Brandon L. Ashfeld. "An umpolung approach toward N-aryl nitrone construction: a phosphine-mediated addition of 1,2-dicarbonyls to nitroso electrophiles." Chem. Commun. 50, no. 74 (2014): 10853–56. http://dx.doi.org/10.1039/c4cc05044d.

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44

Tsukamoto, Hirokazu, Ayumu Kawase, and Takayuki Doi. "Asymmetric palladium-catalyzed umpolung cyclization of allylic acetate-aldehyde using formate as a reductant." Chemical Communications 51, no. 38 (2015): 8027–30. http://dx.doi.org/10.1039/c5cc02176f.

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Asymmetic palladium/chiral diphosphine-catalyzed umpolung cyclization of allylic acetate-aldehyde using formate as a reductant affordscis-disubstituted pyrrolidine, tetrahydrofuran, and spiro carbocycle.

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45

Yatham, Veera Reddy, Jörg-M. Neudörfl, Nils E. Schlörer, and 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, no. 7 (2015): 3706–11. http://dx.doi.org/10.1039/c5sc01027f.

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46

Caramenti, Paola, Nina Declas, Romain Tessier, Matthew D. Wodrich, and Jerome Waser. "Stereoselective synthesis of alkyl-, aryl-, vinyl- and alkynyl-substituted Z-enamides and enol ethers." Chemical Science 10, no. 11 (2019): 3223–30. http://dx.doi.org/10.1039/c8sc05573d.

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47

Niu, Dawen, Liqiang Wan, Lan Tian, and Jie Liu. "Iridium-Catalyzed Asymmetric Umpolung Allylation of N-Fluorenyl Imines to Prepare 1,4-Disubstituted Homoallylic Amines." Synlett 28, no. 16 (August 8, 2017): 2051–56. http://dx.doi.org/10.1055/s-0036-1588514.

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The discovery and development of an Ir-catalyzed asymmetric umpolung allylation of imines is discussed here. This method produces 1,4-disubstituted homoallylic amines, a class of compounds that are difficult to access by conventional methods. This reaction proceeds through a sequence involving an allylation and a 2-aza-Cope rearrangement event. The unique mechanistic feature of this reaction could be the reason for its broad substrate scope. The products of this reaction are useful intermediates for various bioactive and natural products. Besides its immediate synthetic utility, we expect this transformation to inspire the development of other umpolung functionalizations of imines and Ir-catalyzed asymmetric allylic substitution (AAS) reactions.1 Introduction2 Reaction Discovery3 Substrate Scope4 Conclusion

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48

Dong, Ziyang, Chengming Jiang, and Changgui Zhao. "A Review on Generation and Reactivity of the N-Heterocyclic Carbene-Bound Alkynyl Acyl Azolium Intermediates." Molecules 27, no. 22 (November 17, 2022): 7990. http://dx.doi.org/10.3390/molecules27227990.

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N-heterocyclic carbene (NHC) has been widely used as an organocatalyst for both umpolung and non-umpolung chemistry. Previous works mainly focus on species including Breslow intermediate, azolium enolate intermediate, homoenolate intermediate, alkenyl acyl azolium intermediate, etc. Notably, the NHC-bound alkynyl acyl azolium has emerged as an effective intermediate to access functionalized cyclic molecular skeleton until very recently. In this review, we summarized the generation and reactivity of the NHC-bound alkynyl acyl azolium intermediates, which covers the efforts and advances in the synthesis of achiral and axially chiral cyclic scaffolds via the NHC-bound alkynyl acyl azolium intermediates. In particular, the mechanism related to this intermediate is discussed in detail.

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49

Aksenov, Alexander V., Nicolai A. Aksenov, Naila A. Orazova, Dmitrii A. Aksenov, Maksim V. Dmitriev, and Michael Rubin. "Direct metal-free synthesis of diarylamines from 2-nitropropane via the twofold C–H functionalization of arenes." RSC Advances 5, no. 103 (2015): 84849–55. http://dx.doi.org/10.1039/c5ra17668a.

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50

Nie, Guihua, Xuan Huang, Zhongyao Wang, Dingwu Pan, Junmin Zhang, and Yonggui Robin Chi. "Umpolung of donor–acceptor cyclopropanes via N-heterocyclic carbene organic catalysis." Organic Chemistry Frontiers 8, no. 18 (2021): 5105–11. http://dx.doi.org/10.1039/d1qo00826a.

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A carbene-catalyzed formal umpolung of donor–acceptor (D–A) cyclopropanes is disclosed with chiral spirocyclic lactones bearing multiple functional groups afforded with excellent enantio- and diastereoselectivities.

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