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Autor: Grafiati

Data publikacji: 4 czerwca 2021

Data aktualizacji: 25 maja 2024

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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, nr 2 (4.01.2019): 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

Toy, P., i T. But. "Catalytic Mitsunobu Reaction". Synfacts 2006, nr 9 (wrzesień 2006): 0947. http://dx.doi.org/10.1055/s-2006-949230.

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3

Hain, Julia, Patrick Rollin, Werner Klaffke i Thisbe K. Lindhorst. "Anomeric modification of carbohydrates using the Mitsunobu reaction". Beilstein Journal of Organic Chemistry 14 (29.06.2018): 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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4

Kasama, Kengo. "Redox-neutral Mitsunobu Reaction". Journal of Synthetic Organic Chemistry, Japan 79, nr 4 (1.04.2021): 344–45. http://dx.doi.org/10.5059/yukigoseikyokaishi.79.344.

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5

Longwitz, Lars, i Thomas Werner. "The Mitsunobu reaction, reimagined". Science 365, nr 6456 (29.08.2019): 866–67. http://dx.doi.org/10.1126/science.aay6635.

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6

Boyle, Benjamin T., Kyle G. Nottingham i Andrew McNally. "An Organocatalytic Mitsunobu Reaction". Trends in Chemistry 2, nr 2 (luty 2020): 174–75. http://dx.doi.org/10.1016/j.trechm.2019.11.001.

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7

Munawar, Saba, Ameer Fawad Zahoor, Shafaqat Ali, Sadia Javed, Muhammad Irfan, Ali Irfan, Katarzyna Kotwica-Mojzych i Mariusz Mojzych. "Mitsunobu Reaction: A Powerful Tool for the Synthesis of Natural Products: A Review". Molecules 27, nr 20 (17.10.2022): 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

Jia, Zhaozhong J., Sandra Kelberlau, Lars Olsson, G. Anilkumar i Bert Fraser-Reid. "The Mitsunobu Reaction of Tetrachlorophthalimide". Synlett 1999, nr 5 (maj 1999): 565–66. http://dx.doi.org/10.1055/s-1999-2680.

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9

Markowicz, Marcin W., i Roman Dembinski. "Fluorous, Chromatography-Free Mitsunobu Reaction". Organic Letters 4, nr 22 (październik 2002): 3785–87. http://dx.doi.org/10.1021/ol0264511.

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10

HUGHES, D. L. "ChemInform Abstract: The Mitsunobu Reaction". ChemInform 25, nr 44 (18.08.2010): no. http://dx.doi.org/10.1002/chin.199444253.

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11

Grice, I. Darren, Peta J. Harvey, Ian D. Jenkins, Michael J. Gallagher i Millagahamada G. Ranasinghe. "Phosphitylation via the Mitsunobu reaction". Tetrahedron Letters 37, nr 7 (luty 1996): 1087–90. http://dx.doi.org/10.1016/0040-4039(95)02282-1.

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12

Fletcher, S. "The Mitsunobu reaction in the 21st century". Organic Chemistry Frontiers 2, nr 6 (2015): 739–52. http://dx.doi.org/10.1039/c5qo00016e.

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13

Camp, D., i ID Jenkins. "The Reaction of Thiols and α,ω-Dithiols With Triphenylphosphine and Diisopropyl Azodicarboxylate". Australian Journal of Chemistry 43, nr 1 (1990): 161. http://dx.doi.org/10.1071/ch9900161.

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α,ω-Dithiols in the presence of triphenylphosphine and diisopropyl azodicarboxylate are converted into a mixture of monomeric and polymeric disulfides. The product distribution is dependent on the alkyl chain length and the reaction conditions. In contrast to normal Mitsunobu reactions, disulfide bond formation is achieved with regeneration of triphenylphosphine. The mechanism of this reaction is discussed.

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14

Harned, Andrew M., Helen Song He, Patrick H. Toy, Daniel L. Flynn i Paul R. Hanson. "Multipolymer Solution-Phase Reactions: Application to the Mitsunobu Reaction". Journal of the American Chemical Society 127, nr 1 (styczeń 2005): 52–53. http://dx.doi.org/10.1021/ja045188r.

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15

Huang, Yangen, Roger W. Read i Xiaobei Wang. "Efficient Alkylation Methods for the Synthesis of Hybrid Fluorocarbon - Hydrocarbon Tetrazoles as Potential Fluorinated Surfactants". Australian Journal of Chemistry 63, nr 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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16

Seio, Kohji, Munefumi Tokugawa, Kazuhei Kaneko, Takashi Shiozawa i Yoshiaki Masaki. "A Systematic Study of the Synthesis of 2ʹ-Deoxynucleosides by Mitsunobu Reaction". Synlett 28, nr 15 (7.06.2017): 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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17

Ahn, Chuljin, Reuben Correia i Philip DeShong. "Mechanistic Study of the Mitsunobu Reaction". Journal of Organic Chemistry 68, nr 3 (luty 2003): 1176. http://dx.doi.org/10.1021/jo027970k.

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18

Ye, Xin-Shan, Jian Guo, Yu-Jiao Lu i Li Zhang. "Hydrophobically Assisted Separation-Friendly Mitsunobu Reaction". Synlett 23, nr 11 (14.06.2012): 1696–700. http://dx.doi.org/10.1055/s-0031-1290406.

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19

Ahn, Chuljin, Reuben Correia i Philip DeShong. "Mechanistic Study of the Mitsunobu Reaction". Journal of Organic Chemistry 67, nr 6 (marzec 2002): 1751–53. http://dx.doi.org/10.1021/jo001590m.

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20

Manvar, Atul, i Anamik Shah. "Subtle Mitsunobu couplings under super-heating: the role of high-throughput continuous flow and microwave strategies". Org. Biomol. Chem. 12, nr 41 (2014): 8112–24. http://dx.doi.org/10.1039/c4ob01432d.

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21

Bongarzone, S., A. Runser, C. Taddei, A. K. Haji Dheere i A. D. Gee. "From [11C]CO2 to [11C]amides: a rapid one-pot synthesis via the Mitsunobu reaction". Chemical Communications 53, nr 38 (2017): 5334–37. http://dx.doi.org/10.1039/c7cc01407d.

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22

Dai, Chuan, Jun Ma, Min Li, Wen Wu, Xuefeng Xia i Jinqiang Zhang. "Diversity-oriented submonomer synthesis of azapeptides mediated by the Mitsunobu reaction". Organic Chemistry Frontiers 6, nr 14 (2019): 2529–33. http://dx.doi.org/10.1039/c9qo00296k.

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23

Camp, D., i ID Jenkins. "The Mechanism of the Mitsunobu Reaction. III. The Use of Tributylphosphine". Australian Journal of Chemistry 45, nr 1 (1992): 47. http://dx.doi.org/10.1071/ch9920047.

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31P n.m.r . studies indicate that, when tributylphosphine is used in the Mitsunobu esterification reaction, clean formation of a single intermediate, an alkoxyphosphonium carboxylate, is apparent. In the absence of acid, at least two species are observed, a dialkoxytributylphoshorane and the corresponding alkoxyphosphonium salt. The order of mixing of the reagents can dramatically change the mechanism and stereochemistry of esterification reactions.

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24

Tang, Xiaoping, Charlotte Chapman, Matthew Whiting i Ross Denton. "Development of a redox-free Mitsunobu reaction exploiting phosphine oxides as precursors to dioxyphosphoranes". Chem. Commun. 50, nr 55 (2014): 7340–43. http://dx.doi.org/10.1039/c4cc02171a.

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25

Adler, Pauline, Antoine Fadel, Joëlle Prunet i Nicolas Rabasso. "From acyclic to cyclic α-amino vinylphosphonates by using ring-closing metathesis". Organic & Biomolecular Chemistry 15, nr 2 (2017): 387–95. http://dx.doi.org/10.1039/c6ob02548j.

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26

Mujahid, Mohammad, Jambu Subramanian, Viswanadh Nalla, Murugesan Sasikumar, Sunita Sharad Kunte i Murugan Muthukrishnan. "A new and efficient enantioselective synthesis of both enantiomers of the calcium channel blocker bepridil". New Journal of Chemistry 41, nr 2 (2017): 824–29. http://dx.doi.org/10.1039/c6nj02928k.

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27

Sugimoto, Osamu, Tomoyo Arakaki, Hiroka Kamio i 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, nr 55 (2014): 7314–17. http://dx.doi.org/10.1039/c4cc01971g.

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28

Pal, Pratik, Nandan Jana i Samik Nanda. "Asymmetric total synthesis of paecilomycin E, 10′-epi-paecilomycin E and 6′-epi-cochliomycin C". Org. Biomol. Chem. 12, nr 41 (2014): 8257–74. http://dx.doi.org/10.1039/c4ob01400f.

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29

Holzer, Wolfgang, Brigitte Plagens i Karin Lorenz. "Alkylation of Pyrazolones via the Mitsunobu Reaction". HETEROCYCLES 45, nr 2 (1997): 309. http://dx.doi.org/10.3987/com-96-7657.

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30

Varasi, Mario, Keith A. M. Walker i Michael L. Maddox. "A revised mechanism for the Mitsunobu reaction". Journal of Organic Chemistry 52, nr 19 (wrzesień 1987): 4235–38. http://dx.doi.org/10.1021/jo00228a016.

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31

Camp, David, Graeme R. Hanson i Ian D. Jenkins. "Formation of Radicals in the Mitsunobu Reaction". Journal of Organic Chemistry 60, nr 10 (maj 1995): 2977–80. http://dx.doi.org/10.1021/jo00115a011.

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32

Hughes, David L. "PROGRESS IN THE MITSUNOBU REACTION. A REVIEW". Organic Preparations and Procedures International 28, nr 2 (kwiecień 1996): 127–64. http://dx.doi.org/10.1080/00304949609356516.

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33

Yoakim, Christiane, I. Guse, J. A. O’Meara i B. Thavonekham. "Removable Phosphine Reagents for the Mitsunobu Reaction". Synlett, nr 4 (2003): 0473–76. http://dx.doi.org/10.1055/s-2003-37520.

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34

Huang, Hai, i Jun Yong Kang. "Mitsunobu Reaction Using Basic Amines as Pronucleophiles". Journal of Organic Chemistry 82, nr 13 (15.06.2017): 6604–14. http://dx.doi.org/10.1021/acs.joc.7b00622.

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35

Pokluda, Adam, Michal Kohout, Josef Chudoba, Martin Krupička i Radek Cibulka. "Nitrosobenzene: Reagent for the Mitsunobu Esterification Reaction". ACS Omega 4, nr 3 (7.03.2019): 5012–18. http://dx.doi.org/10.1021/acsomega.8b03551.

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36

Harvey, Peta J., i Ian D. Jenkins. "Synthesis of fluorophosphoranes via the mitsunobu reaction". Tetrahedron Letters 35, nr 52 (grudzień 1994): 9775–78. http://dx.doi.org/10.1016/0040-4039(94)88383-1.

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37

Hovinen, Jari, i Reijo Sillanpää. "Synthesis of azamacrocycles via a Mitsunobu reaction". Tetrahedron Letters 46, nr 25 (czerwiec 2005): 4387–89. http://dx.doi.org/10.1016/j.tetlet.2005.04.078.

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38

Schenk, Stephan, Jennie Weston i Ernst Anders. "Density Functional Investigation of the Mitsunobu Reaction". Journal of the American Chemical Society 127, nr 36 (wrzesień 2005): 12566–76. http://dx.doi.org/10.1021/ja052362i.

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39

Szlenkier, Maurycy, Karol Kamel i Jerzy Boryski. "Regioselective Mitsunobu Reaction of Partially Protected Uridine". Nucleosides, Nucleotides & Nucleic Acids 35, nr 8 (28.06.2016): 410–25. http://dx.doi.org/10.1080/15257770.2016.1188943.

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40

Shull, Brian K., Takashi Sakai, Jeffrey B. Nichols i Masato Koreeda. "Mitsunobu Reaction of Unbiased Cyclic Allylic Alcohols". Journal of Organic Chemistry 62, nr 24 (listopad 1997): 8294–303. http://dx.doi.org/10.1021/jo9615155.

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41

Jia, Zhaozhong J., Sandra Kelberlau, Lars Olsson, G. Anilkumar i Bert Fraser-Reid. "ChemInform Abstract: The Mitsunobu Reaction of Tetrachlorophthalimide." ChemInform 30, nr 38 (13.06.2010): no. http://dx.doi.org/10.1002/chin.199938133.

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42

GRICE, I. D., P. J. HARVEY, I. D. JENKINS, M. J. GALLAGHER i M. G. RANASINGHE. "ChemInform Abstract: Phosphitylation via the Mitsunobu Reaction." ChemInform 27, nr 22 (5.08.2010): no. http://dx.doi.org/10.1002/chin.199622185.

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43

Hirose, Daisuke, Martin Gazvoda, Janez Košmrlj i Tsuyoshi Taniguchi. "Advances and mechanistic insight on the catalytic Mitsunobu reaction using recyclable azo reagents". Chemical Science 7, nr 8 (2016): 5148–59. http://dx.doi.org/10.1039/c6sc00308g.

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44

Beddoe, Rhydian H., Helen F. Sneddon i Ross M. Denton. "The catalytic Mitsunobu reaction: a critical analysis of the current state-of-the-art". Organic & Biomolecular Chemistry 16, nr 42 (2018): 7774–81. http://dx.doi.org/10.1039/c8ob01929k.

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45

Hanaya, Tadashi, Kiyoshi Torigoe, Kazuyuki Soranaka, Horoshi Yamamoto, Yao Qizhengt i Wolfgang Pfleiderer. "Pteridines CV". Pteridines 6, nr 1 (luty 1995): 1–7. http://dx.doi.org/10.1515/pteridines.1995.6.1.1.

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Summary Treatment of L-biopterin (I) with N,N-dimethyformamide dimethyl- (or diethyl)acetal and then with acetic anhydride in pyridine gave 1',2'-di-O-acetyl-N'-(N,N-dimethylaminomethylene)-L-biopterin (4), which was converted by the Mitsunobu reaction into 3-methyl (5) and 3-p-nitrophenetyl derivatives (7). The protective groups on the side chain diols and N2 of these compounds were selectively cleaved to furnish products 6, 8-10, among which 9 is naturally occurring 3-methyl-L-biopterin and 8 is N',N(3)-protected biopterin, a versatile intermediate for various reactions on the side-chain diol. In contrast, the same Mitsunobu reactions of tri-N2:I',2'-0-acetyl-L-biopterin (II) afforded 04-methyl (12) and 04-NPE derivatives (13), both of which yielded 0 4-methyl-L-biopterin (14) and subsequently led to 4-amino-L-biopterin (18).

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46

B., Unterhalt, i Adam T. "1-(4-Biphenylyl)ethylnitramine, bioisostere Profene". Scientia Pharmaceutica 70, nr 4 (5.12.2002): 353–58. http://dx.doi.org/10.3797/scipharm.aut-02-34.

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47

Serpico, Luigia, Mauro De Nisco, Flavio Cermola, Michele Manfra i Silvana Pedatella. "Stereoselective Synthesis of Selenium-Containing Glycoconjugates via the Mitsunobu Reaction". Molecules 26, nr 9 (27.04.2021): 2541. http://dx.doi.org/10.3390/molecules26092541.

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A simple and efficient route for the synthesis of new glycoconjugates has been developed. The approach acts as a model for a mini-library of compounds with a deoxy-selenosugar core joined to a polyphenolic moiety with well-known antioxidant properties. An unexpected stereocontrol detected in the Mitsunobu key reaction led to the most attractive product showing a natural d-configuration. Thus, we were able to obtain the target molecules from the commercially available d-ribose via a shorter and convenient sequence of reactions.

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48

Ligi, Maria Cristina, Anna Flis, Giacomo Biagiotti, Giulia Serrano, K. Michał Pietrusiewicz i Stefano Cicchi. "Heterogeneous Organo- and Metal Catalysis Using Phosphine Oxide Derivatives Anchored on Multiwalled Carbon Nanotubes". C—Journal of Carbon Research 6, nr 3 (21.09.2020): 57. http://dx.doi.org/10.3390/c6030057.

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Oxidized multiwalled carbon nanotubes were modified anchoring phosphine oxides and used as heterogeneous catalysts. A proper substitution of the phosphine oxides allowed the use of the Tour reaction and the nitrene cycloaddition to obtain functionalized carbon nanotubes (CNT) with a loading up to 0.73 mmol/g of material. The catalysts proved efficient in Wittig reactions, Mitsunobu reactions, and Staudinger ligations. Furthermore, the phosphorus decorated CNT were used to produce nanocomposite with Pd nanoparticles able to catalyze Heck reactions.

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49

Burns, Michael J., Thomas O. Ronson, Richard J. K. Taylor i Ian J. S. Fairlamb. "4-Hydroxy-6-alkyl-2-pyrones as nucleophilic coupling partners in Mitsunobu reactions and oxa-Michael additions". Beilstein Journal of Organic Chemistry 10 (20.05.2014): 1159–65. http://dx.doi.org/10.3762/bjoc.10.116.

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Two mild and efficient strategies have been developed for the O-functionalisation of 4-hydroxy-6-alkyl-2-pyrones, by using them as nucleophilic partners in oxa-Michael additions and the Mitsunobu reaction. The reactions proceed in moderate to excellent yields on a range of substrates containing useful functionality. The reactions serve as practical and valuable synthetic methods to construct complex 2-pyronyl ethers, which are found embedded in a number of natural products.

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50

Brulikova, L., Y. Okorochenkova i J. Hlavac. "A solid-phase synthetic approach to pH-independent rhodamine-type fluorophores". Organic & Biomolecular Chemistry 14, nr 44 (2016): 10437–43. http://dx.doi.org/10.1039/c6ob01772j.

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