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Journal articles on the topic 'Mitsunobu'

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Author: Grafiati

Published: 4 June 2021

Last updated: 20 February 2023

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1

Panday, Sharad Kumar. "Advances in the Mitsunobu Reaction: An Excellent Organic Protocol with Versatile Applications." Mini-Reviews in Organic Chemistry 16, no. 2 (January 4, 2019): 127–40. http://dx.doi.org/10.2174/1570193x15666180612090313.

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The beginning of 1970’s may well be regarded as turning point in the area of organic synthesis when an efficient and straight forward strategy for the reaction of primary and/or secondary alcohols with variety of nucleophiles in the presence of triphenylphosphine and azodicarboxylate reagent was discovered by O. Mitsunobu and since then rapid progress has been made in understanding and applying the Mitsunobu reaction for various derivatization reactions. Due to versatile applications and mild reaction conditions associated with the said strategy, the Mitsunobu reaction has received much attention in the last almost fifty years and has been well reported. The basic objective of this review is to pay attention on the recent advances and applications of the Mitsunobu reaction particularly in last decade. The attention has also been paid to describe various modifications which have been explored in the traditional Mitsunobu reaction by substituting P (III) reagents or azodicarboxylate reagents with other suitable reagents or else using an organocatalyst with the objective to improve upon the traditional Mitsunobu reaction. In the present review we wish to report the major advancements achieved in last few years which are likely to be beneficial for the researchers across the globe.

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2

Hain, Julia, Patrick Rollin, Werner Klaffke, and Thisbe K. Lindhorst. "Anomeric modification of carbohydrates using the Mitsunobu reaction." Beilstein Journal of Organic Chemistry 14 (June 29, 2018): 1619–36. http://dx.doi.org/10.3762/bjoc.14.138.

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The Mitsunobu reaction basically consists in the conversion of an alcohol into an ester under inversion of configuration, employing a carboxylic acid and a pair of two auxiliary reagents, mostly triphenylphosphine and a dialkyl azodicarboxylate. This reaction has been frequently used in carbohydrate chemistry for the modification of sugar hydroxy groups. Modification at the anomeric position, leading mainly to anomeric esters or glycosides, is of particular importance in the glycosciences. Therefore, this review focuses on the use of the Mitsunobu reaction for modifications of sugar hemiacetals. Strikingly, unprotected sugars can often be converted regioselectively at the anomeric center, whereas in other cases, the other hydroxy groups in reducing sugars have to be protected to achieve good results in the Mitsunobu procedure. We have reviewed on the one hand the literature on anomeric esterification, including glycosyl phosphates, and on the other hand glycoside synthesis, including S- and N-glycosides. The mechanistic details of the Mitsunobu reaction are discussed as well as this is important to explain and predict the stereoselectivity of anomeric modifications under Mitsunobu conditions. Though the Mitsunobu reaction is often not the first choice for the anomeric modification of carbohydrates, this review shows the high value of the reaction in many different circumstances.

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3

Bianchi, Darío A., and Teodoro S. Kaufman. "A tosyliminium ion-based total synthesis of (±)-schefferine." Canadian Journal of Chemistry 78, no. 9 (September 1, 2000): 1165–69. http://dx.doi.org/10.1139/v00-120.

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The synthesis of the phenolic tetrahydroprotoberberine alkaloid (±)-schefferine is reported, featuring as key steps a tosyliminium ion-mediated Friedel-Crafts alkylation of eugenol dimethyl ether and an intramolecular Mitsunobu-type amination.Key words: total synthesis, (±)-schefferine, natural product, tosyliminium ion, Mitsunobu amination.

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4

But, Tracy Yuen Sze, and Patrick H. Toy. "Organocatalytic Mitsunobu Reactions." Journal of the American Chemical Society 128, no. 30 (August 2006): 9636–37. http://dx.doi.org/10.1021/ja063141v.

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5

Toy, P., and T. But. "Catalytic Mitsunobu Reaction." Synfacts 2006, no. 9 (September 2006): 0947. http://dx.doi.org/10.1055/s-2006-949230.

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6

Davey, Stephen. "Mitsunobu minus waste." Nature Chemistry 5, no. 5 (April 23, 2013): 358. http://dx.doi.org/10.1038/nchem.1639.

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7

Munawar, Saba, Ameer Fawad Zahoor, Shafaqat Ali, Sadia Javed, Muhammad Irfan, Ali Irfan, Katarzyna Kotwica-Mojzych, and Mariusz Mojzych. "Mitsunobu Reaction: A Powerful Tool for the Synthesis of Natural Products: A Review." Molecules 27, no. 20 (October 17, 2022): 6953. http://dx.doi.org/10.3390/molecules27206953.

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The Mitsunobu reaction plays a vital part in organic chemistry due to its wide synthetic applications. It is considered as a significant reaction for the interconversion of one functional group (alcohol) to another (ester) in the presence of oxidizing agents (azodicarboxylates) and reducing agents (phosphines). It is a renowned stereoselective reaction which inverts the stereochemical configuration of end products. One of the most important applications of the Mitsunobu reaction is its role in the synthesis of natural products. This review article will focus on the contribution of the Mitsunobu reaction towards the total synthesis of natural products, highlighting their biological potential during recent years.

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8

Cisneros Pérez, Pablo A., and Bernardo A. Fontana Uribe. "Síntesis de Sistemas bis-tiofénicos con puente α,α’-dioxi-m-xileno." Química Central 3, no. 2 (September 27, 2017): 11–18. http://dx.doi.org/10.29166/quimica.v3i2.1208.

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Las reacciones de formación de aril-alquil éteres mediante las reacciones de Mitsunobu y de Williamson fueron evaluadas en la síntesis de sistemas bis-tiofénicos con puente α,α’-dioxi-m-xileno. Se obtuvieron rendimientos más altos y una purificación más fácil al utilizar la metodología de Mitsunobu en baño sónico.

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9

Huang, Yangen, Roger W. Read, and Xiaobei Wang. "Efficient Alkylation Methods for the Synthesis of Hybrid Fluorocarbon - Hydrocarbon Tetrazoles as Potential Fluorinated Surfactants." Australian Journal of Chemistry 63, no. 5 (2010): 802. http://dx.doi.org/10.1071/ch10005.

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The first 1,5- and 2,5-disubstituted fluorous tetrazoles are sought as potential surfactants. Direct alkylation of monosubstituted tetrazoles using alkyl iodides and triflates is compared with the Mitsunobu reaction. Mitsunobu conditions provide advantage for perfluoroalkylethylation, in terms of selectivity towards the 2,5-isomers and overall yield, but are not applicable to perfluoroalkylmethylation.

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10

Kasama, Kengo. "Redox-neutral Mitsunobu Reaction." Journal of Synthetic Organic Chemistry, Japan 79, no. 4 (April 1, 2021): 344–45. http://dx.doi.org/10.5059/yukigoseikyokaishi.79.344.

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11

Longwitz, Lars, and Thomas Werner. "The Mitsunobu reaction, reimagined." Science 365, no. 6456 (August 29, 2019): 866–67. http://dx.doi.org/10.1126/science.aay6635.

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12

McNally, Andy. "Mitsunobu gets a makeover." Nature Chemistry 11, no. 11 (October 11, 2019): 966–67. http://dx.doi.org/10.1038/s41557-019-0362-2.

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13

Boyle, Benjamin T., Kyle G. Nottingham, and Andrew McNally. "An Organocatalytic Mitsunobu Reaction." Trends in Chemistry 2, no. 2 (February 2020): 174–75. http://dx.doi.org/10.1016/j.trechm.2019.11.001.

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14

Seio, Kohji, Munefumi Tokugawa, Kazuhei Kaneko, Takashi Shiozawa, and Yoshiaki Masaki. "A Systematic Study of the Synthesis of 2ʹ-Deoxynucleosides by Mitsunobu Reaction." Synlett 28, no. 15 (June 7, 2017): 2014–17. http://dx.doi.org/10.1055/s-0036-1588445.

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The Mitsunobu reaction has emerged as an important alternative for the preparation of synthetic 2′-deoxynucleosides, which have various biological and biotechnological applications. In this work, the Mitsunobu-based synthesis of 2′-deoxynucleosides was systematically studied. The effect of phosphine, azodicarbonyl reagent, and solvent on the product yield and α/β ratio was investigated, and the highest yield and β-selectivity were obtained using (n-Bu)3P and 1,1′-(azodicarbonyl)dipiperidine in DMF. The reaction was successfully applied to various nucleobase analogues.

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15

Manvar, Atul, and Anamik Shah. "Subtle Mitsunobu couplings under super-heating: the role of high-throughput continuous flow and microwave strategies." Org. Biomol. Chem. 12, no. 41 (2014): 8112–24. http://dx.doi.org/10.1039/c4ob01432d.

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16

Bongarzone, S., A. Runser, C. Taddei, A. K. Haji Dheere, and A. D. Gee. "From [11C]CO2 to [11C]amides: a rapid one-pot synthesis via the Mitsunobu reaction." Chemical Communications 53, no. 38 (2017): 5334–37. http://dx.doi.org/10.1039/c7cc01407d.

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17

Hirose, Daisuke, Tsuyoshi Taniguchi, and Hiroyuki Ishibashi. "Recyclable Mitsunobu Reagents: Catalytic Mitsunobu Reactions with an Iron Catalyst and Atmospheric Oxygen." Angewandte Chemie International Edition 52, no. 17 (March 6, 2013): 4613–17. http://dx.doi.org/10.1002/anie.201300153.

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18

Hirose, Daisuke, Tsuyoshi Taniguchi, and Hiroyuki Ishibashi. "Recyclable Mitsunobu Reagents: Catalytic Mitsunobu Reactions with an Iron Catalyst and Atmospheric Oxygen." Angewandte Chemie 125, no. 17 (March 6, 2013): 4711–15. http://dx.doi.org/10.1002/ange.201300153.

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19

Tang, Xiaoping, Charlotte Chapman, Matthew Whiting, and Ross Denton. "Development of a redox-free Mitsunobu reaction exploiting phosphine oxides as precursors to dioxyphosphoranes." Chem. Commun. 50, no. 55 (2014): 7340–43. http://dx.doi.org/10.1039/c4cc02171a.

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20

Fletcher, S. "The Mitsunobu reaction in the 21st century." Organic Chemistry Frontiers 2, no. 6 (2015): 739–52. http://dx.doi.org/10.1039/c5qo00016e.

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21

TSUNODA, Tetsuto, and Shô ITÔ. "Development of New Mitsunobu Reagents." Journal of Synthetic Organic Chemistry, Japan 55, no. 7 (1997): 631–41. http://dx.doi.org/10.5059/yukigoseikyokaishi.55.631.

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22

Beddoe, Rhydian H., Keith G. Andrews, Valentin Magné, James D. Cuthbertson, Jan Saska, Andrew L. Shannon-Little, Stephen E. Shanahan, Helen F. Sneddon, and Ross M. Denton. "Redox-neutral organocatalytic Mitsunobu reactions." Science 365, no. 6456 (August 29, 2019): 910–14. http://dx.doi.org/10.1126/science.aax3353.

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Nucleophilic substitution reactions of alcohols are among the most fundamental and strategically important transformations in organic chemistry. For over half a century, these reactions have been achieved by using stoichiometric, and often hazardous, reagents to activate the otherwise unreactive alcohols. Here, we demonstrate that a specially designed phosphine oxide promotes nucleophilic substitution reactions of primary and secondary alcohols in a redox-neutral catalysis manifold that produces water as the sole by-product. The scope of the catalytic coupling process encompasses a range of acidic pronucleophiles that allow stereospecific construction of carbon-oxygen and carbon-nitrogen bonds.

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23

Jia, Zhaozhong J., Sandra Kelberlau, Lars Olsson, G. Anilkumar, and Bert Fraser-Reid. "The Mitsunobu Reaction of Tetrachlorophthalimide." Synlett 1999, no. 5 (May 1999): 565–66. http://dx.doi.org/10.1055/s-1999-2680.

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24

Markowicz, Marcin W., and Roman Dembinski. "Fluorous, Chromatography-Free Mitsunobu Reaction." Organic Letters 4, no. 22 (October 2002): 3785–87. http://dx.doi.org/10.1021/ol0264511.

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25

Dandapani, Sivaraman, and Dennis P. Curran. "Fluorous Mitsunobu reagents and reactions." Tetrahedron 58, no. 20 (May 2002): 3855–64. http://dx.doi.org/10.1016/s0040-4020(02)00205-3.

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26

HUGHES, D. L. "ChemInform Abstract: The Mitsunobu Reaction." ChemInform 25, no. 44 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199444253.

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27

Grice, I. Darren, Peta J. Harvey, Ian D. Jenkins, Michael J. Gallagher, and Millagahamada G. Ranasinghe. "Phosphitylation via the Mitsunobu reaction." Tetrahedron Letters 37, no. 7 (February 1996): 1087–90. http://dx.doi.org/10.1016/0040-4039(95)02282-1.

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28

Beddoe, Rhydian H., Helen F. Sneddon, and Ross M. Denton. "The catalytic Mitsunobu reaction: a critical analysis of the current state-of-the-art." Organic & Biomolecular Chemistry 16, no. 42 (2018): 7774–81. http://dx.doi.org/10.1039/c8ob01929k.

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29

Dai, Chuan, Jun Ma, Min Li, Wen Wu, Xuefeng Xia, and Jinqiang Zhang. "Diversity-oriented submonomer synthesis of azapeptides mediated by the Mitsunobu reaction." Organic Chemistry Frontiers 6, no. 14 (2019): 2529–33. http://dx.doi.org/10.1039/c9qo00296k.

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30

Chen, Chen, Xi-wen Geng, Ya-hui Pan, Yu-ning Ma, Yu-xia Ma, Shu-zhong Gao, and Xiao-jun Huang. "Synthesis and characterization of tannic acid–PEG hydrogel via Mitsunobu polymerization." RSC Advances 10, no. 3 (2020): 1724–32. http://dx.doi.org/10.1039/c9ra09229c.

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31

Hirose, Daisuke, Tsuyoshi Taniguchi, and Hiroyuki Ishibashi. "Berichtigung: Recyclable Mitsunobu Reagents: Catalytic Mitsunobu Reactions with an Iron Catalyst and Atmospheric Oxygen." Angewandte Chemie 127, no. 13 (March 16, 2015): 3917. http://dx.doi.org/10.1002/ange.201501188.

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32

Hirose, Daisuke, Tsuyoshi Taniguchi, and Hiroyuki Ishibashi. "Corrigendum: Recyclable Mitsunobu Reagents: Catalytic Mitsunobu Reactions with an Iron Catalyst and Atmospheric Oxygen." Angewandte Chemie International Edition 54, no. 13 (March 16, 2015): 3847. http://dx.doi.org/10.1002/anie.201501188.

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33

Usman, Muhammad, Xiao-Wen Zhang, Di Wu, Zheng-Hui Guan, and Wen-Bo Liu. "Application of dialkyl azodicarboxylate frameworks featuring multi-functional properties." Organic Chemistry Frontiers 6, no. 11 (2019): 1905–28. http://dx.doi.org/10.1039/c9qo00017h.

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34

Hirose, Daisuke, Martin Gazvoda, Janez Košmrlj, and Tsuyoshi Taniguchi. "Advances and mechanistic insight on the catalytic Mitsunobu reaction using recyclable azo reagents." Chemical Science 7, no. 8 (2016): 5148–59. http://dx.doi.org/10.1039/c6sc00308g.

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35

Adler, Pauline, Antoine Fadel, Joëlle Prunet, and Nicolas Rabasso. "From acyclic to cyclic α-amino vinylphosphonates by using ring-closing metathesis." Organic & Biomolecular Chemistry 15, no. 2 (2017): 387–95. http://dx.doi.org/10.1039/c6ob02548j.

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36

Mujahid, Mohammad, Jambu Subramanian, Viswanadh Nalla, Murugesan Sasikumar, Sunita Sharad Kunte, and Murugan Muthukrishnan. "A new and efficient enantioselective synthesis of both enantiomers of the calcium channel blocker bepridil." New Journal of Chemistry 41, no. 2 (2017): 824–29. http://dx.doi.org/10.1039/c6nj02928k.

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37

Sugimoto, Osamu, Tomoyo Arakaki, Hiroka Kamio, and Ken-ichi Tanji. "The use of a Mitsunobu reagent for the formation of heterocycles: a simple method for the preparation of 3-alkyl-5-aryl-1,3,4-oxadiazol-2(3H)-ones from carboxylic acids." Chem. Commun. 50, no. 55 (2014): 7314–17. http://dx.doi.org/10.1039/c4cc01971g.

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38

Pal, Pratik, Nandan Jana, and Samik Nanda. "Asymmetric total synthesis of paecilomycin E, 10′-epi-paecilomycin E and 6′-epi-cochliomycin C." Org. Biomol. Chem. 12, no. 41 (2014): 8257–74. http://dx.doi.org/10.1039/c4ob01400f.

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39

Qian, Wen-Jian, and Terrence R. Burke. "Mitsunobu mischief: neighbor-directed histidine N(τ)-alkylation provides access to peptides containing selectively functionalized imidazolium heterocycles." Organic & Biomolecular Chemistry 13, no. 14 (2015): 4221–25. http://dx.doi.org/10.1039/c5ob00171d.

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40

Kato, Terumasa, Shin-ichi Matsuoka, and Masato Suzuki. "N-Heterocyclic carbene-mediated redox condensation of alcohols." Chemical Communications 52, no. 55 (2016): 8569–72. http://dx.doi.org/10.1039/c6cc04154j.

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41

B., Unterhalt, and Adam T. "1-(4-Biphenylyl)ethylnitramine, bioisostere Profene." Scientia Pharmaceutica 70, no. 4 (December 5, 2002): 353–58. http://dx.doi.org/10.3797/scipharm.aut-02-34.

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42

Taniguchi, Tsuyoshi. "Development of Mitsunobu Reagents Recyclable by Aerobic Oxidation and the Application to Catalytic Mitsunobu Reactions." Journal of Synthetic Organic Chemistry, Japan 77, no. 6 (June 1, 2019): 584–95. http://dx.doi.org/10.5059/yukigoseikyokaishi.77.584.

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43

Hirose, Daisuke, Tsuyoshi Taniguchi, and Hiroyuki Ishibashi. "ChemInform Abstract: Recyclable Mitsunobu Reagents: Catalytic Mitsunobu Reactions with an Iron Catalyst and Atmospheric Oxygen." ChemInform 44, no. 38 (August 30, 2013): no. http://dx.doi.org/10.1002/chin.201338044.

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44

Brulikova, L., Y. Okorochenkova, and J. Hlavac. "A solid-phase synthetic approach to pH-independent rhodamine-type fluorophores." Organic & Biomolecular Chemistry 14, no. 44 (2016): 10437–43. http://dx.doi.org/10.1039/c6ob01772j.

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45

Indusegaram, Sutharsiny, Andrew G. Katsifis, Damon D. Ridley, and Simone C. Vonwiller. "Nitrogen versus Oxygen Group Protection in Hydroxypropylbenzimidazoles." Australian Journal of Chemistry 56, no. 8 (2003): 819. http://dx.doi.org/10.1071/ch03012.

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In order to convert 1′H-benzimidazol-2′-ylpropanols into aryl ethers using Mitsunobu coupling, it was necessary to protect the benzimidazole nitrogen in the starting alcohols. Selective protection at nitrogen was achieved through N-benzyl derivatives, but attempts to protect the nitrogen directly through tert-butoxycarbonyl, acetyl, trityl, or tetrahydropyranyl derivatives were complicated either by selective reactions at oxygen or by the formation of bis-protected compounds. Transformations of some oxygen-protected derivatives are discussed, and in particular the conversion of the acetates of 1′H-benzimidazol-2′-ylpropanols to N-tetrahydropyranyl derivatives is described. Mitsunobu coupling involving the N-benzyl and N-tetrahydropyranyl derivatives and methyl 4-hydroxybenzoate were achieved, and thus afforded synthetic routes to the desired propylbenzimidazole aryl ethers.

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46

Beddoe, Rhydian H., Daniel C. Edwards, Louis Goodman, Helen F. Sneddon, and Ross M. Denton. "Synthesis of 18O-labelled alcohols from unlabelled alcohols." Chemical Communications 56, no. 48 (2020): 6480–83. http://dx.doi.org/10.1039/d0cc02855j.

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47

Lin, Cheng-Kun, Wei Lee, Chun-Fu Wu, and Fang-Yi Shih. "Recyclable and reusable ionic liquid-supported azo precursors in Mitsunobu reactions." Organic & Biomolecular Chemistry 20, no. 11 (2022): 2217–21. http://dx.doi.org/10.1039/d2ob00039c.

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48

Zhao, Hongyi, Wenting Zhao, Shihao Cheng, Haijia Lu, Dongfeng Zhang, and Haihong Huang. "Efficient and stereoselective one-pot synthesis of benzo[b]oxazolo[3,4-d][1,4]oxazin-1-ones." RSC Advances 10, no. 40 (2020): 24037–44. http://dx.doi.org/10.1039/d0ra04104a.

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49

Boureghda, Chaima, Aurélie Macé, Fabienne Berrée, Thierry Roisnel, Abdelmadjid Debache, and Bertrand Carboni. "Ene reactions of 2-borylated α-methylstyrenes: a practical route to 4-methylenechromanes and derivatives." Organic & Biomolecular Chemistry 17, no. 23 (2019): 5789–800. http://dx.doi.org/10.1039/c9ob00963a.

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4-Methylenechromanes were prepared via a three-step process from 2-borylated α-methylstyrenes using a glyoxylate-ene reaction catalyzed by scandium(iii) triflate and Mitsunobu cyclization as key steps.

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50

García-Rubiño, M. E., M. C. Núñez-Carretero, D. Choquesillo-Lazarte, J. M. García-Ruiz, Yolanda Madrid, and J. M. Campos. "Stereospecific alkylation of substituted adenines by the Mitsunobu coupling reaction under microwave-assisted conditions." RSC Adv. 4, no. 43 (2014): 22425–33. http://dx.doi.org/10.1039/c4ra01968g.

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The Mitsunobu reaction under microwave-assisted conditions reveals a complete inversion of the stereogenic centre of the secondary alcohol giving an alkylated purine linked to a homochiral six-membered ring.

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