Relevant bibliographies by topics / Mitsunobu

Academic literature on the topic 'Mitsunobu'

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Published: 4 June 2021
Last updated: 20 February 2023

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Journal articles on the topic "Mitsunobu"

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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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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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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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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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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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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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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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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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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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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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Dissertations / Theses on the topic "Mitsunobu"

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But, Yuen-sze Tracy, and 畢婉詩. "Organocatalytic alcohol oxidation and Mitsunobu reactions." Thesis, The University of Hong Kong (Pokfulam, Hong Kong), 2009. http://hub.hku.hk/bib/B42182578.

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But, Yuen-sze Tracy. "Organocatalytic alcohol oxidation and Mitsunobu reactions." Click to view the E-thesis via HKUTO, 2009. http://sunzi.lib.hku.hk/hkuto/record/B42182578.

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Camp, David. "Some Aspects of the Mitsunobu Reaction." Thesis, Griffith University, 1990. http://hdl.handle.net/10072/366203.

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A 31P NMR based study of the Mitsunobu esterification reaction has been undertaken. Three intermediates have been identified: an alkoxytriphenyiphosphonium carboxylate, a dialkoxytriphenyiphosphorane and an (acyloxy)alkoxytriphenylphosphorane. These three species are in equilibrium with each other, the position of the various equilibria depending on the polarity of the solvent, pKa of the acid and structure of the alcohol. Given the choice between a primary and secondary alcohol, only the phosphorane and oxyphosphonium salt corresponding to the primary alcohol are observed. The implications of these findings for the regioselectivity and stereoselectivity of the Mitsunobu reaction are discussed. Formation of the phosphonium salt is facilitated in more polar solvents or with acids of low pKa. The chemical shift of the alkoxyphosphonium carboxylate was found to be extraordinarily sensitive to the presence of proton sources and solvent, varying over a range of more than 100 ppm. The peripatetic nature of this species has been interpreted in terms of a rapid equilibrium between the alkoxytriphenylphosphonium carboxylate and the corresponding (acyloxy)alkoxytriphenylphosphorane. Substitution of triphenylphosphine by tributylphosphine using otherwise standard Mitsunobu protocol revealed clean formation of a single intermediate, the alkoxyphosphonium carboxylate. In the absence of acid, at least two species were observed, a dialkoxyphosphorane and an alkoxyphosphonium alkoxide salt. Replacement of iriphenylphosphine by 9-phenyl-9-phosphafluorene confirmed that betaine formation was irreversible and proceeded via a nucleophiic addition, not a cheleotropic mechanism. Modification of triphenylphosphine by incorporation of an alcoholic or acidic moiety into the structure allowed detection of a possible O,Nphosphorane, an intermediate previously postulated in the Mitsunobu reaction. The synthesis of a series of bulky phosphines showed that steric congestion about the phosphonis atom retarded the rate of betaine (and particularly) phosphorane formation. An EPR based study has revealed for the first time that radicals are formed during the reaction of phosphines with azodicarboxylates. Evidence is presented to suggest that the betaine arising from this reaction may be formed via a single electron transfer pathway. The reaction of diphenylphosphine and of diphenylphosphine oxide with azodicarboxylates is examined. Diphenylphosphine reacts surprisingly sluggishly, whereas diphenyiphosphine oxide reacts rapidly to give the expected addition product. An 'abnormal' Mitsunobu-like reaction involving catalytic amounts of triphenylphosphine in the presence of diisopropyl azodicarboxylate and a,co-dithiols to afford disulfides has been studied. The mechanism is discused in terms of expulsion of triphenyiphosphine from either an S,S-dithiophosphorane or thiophosphonium thiolate salt. The substitution of a,w-dithiols by a,w-mercaptoalcohols was also briefly examined. Finally, diphenyl(2-pyridyl)phosphine was used in place of triphenylphosphine for those Mitsunobu reactions where removal of wiphenylphosphine oxide is difficult or troublesome.
Thesis (PhD Doctorate)
Doctor of Philosophy (PhD)
Division of Science and Technology
Science, Environment, Engineering and Technology
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4

Shannon-Little, Andrew Laurence. "Studies towards a phosphorus(V)-catalysed Mitsunobu reaction." Thesis, University of Nottingham, 2016. http://eprints.nottingham.ac.uk/33038/.

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A novel manifold has been developed, catalytic in phosphorus (V), that promotes the dehydration reaction of an alcohol to give the symmetrical ether product. This has been achieved through the development of a novel dioxyphosphorane catalyst that, in conjunction with a triflic acid cocatalyst, conducts the coupling reaction without the need for any additional stoichiometric reagents. This has allowed the omission of the explosive diazo-compounds that are required in the widely-accepted Mitsunobu conditions, and has reduced the amount of inconvenient and difficult-to-remove phosphorus waste that is usually associated with phosphorus-mediated reactions. This work constitutes the first example of a phosphorus (V)-catalysed Mitsunobu-type etherification reaction.
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Le, Foll Alexandra. "Polymères à empreintes moléculaires : nouveaux outils prometteurs pour la synthèse organique." Thesis, Rouen, INSA, 2010. http://www.theses.fr/2010ISAM0006.

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Le projet présenté dans ce manuscrit consiste à utiliser la technologie des polymères à empreintes moléculaires (MIPs) pour concevoir de nouveaux outils pour la synthèse organique. Dans un premier temps, nous nous sommes intéressés à l'étude du potentiel des MIPs en organocatalyse, par l'intermédiaire d'une activation entropique dans les empreintes. Pour cela, plusieurs organocatalyseurs de type quinine thiourée ont été synthétisés afin d'être intégrés dans les cavités du polymère. Malgré l'efficacité de l'impression montrée en HPLC, aucun effet bénéfique sur la vitesse ou l'énantiosélectivité de la réaction n'a pu être mis en évidence par l'utilisation des différents MIPs synthétisés dans la catalyse de la réaction de Henry. Dans un second temps, nous avons développé une stratégie de séparation efficace et applicable à une large gamme de composés en utilisant la technologie des MIPs associées à celle des tags. Notre tag a été formé par réaction de "chimie click" générant ainsi un groupement triazole reconnaissable par un MIP-Tag. Après avoir montré l'efficacité et la sélectivité du MIP-Tag pour une famille de triazoles, l'extraction sélective de la tyrosine taggée d'un mélange d'acides aminés a été réalisée avec une très bonne sélectivité. Par la suite, l'application de notre procédé au recyclage de catalyseurs dérivés de pybox et de proline a été étudiée. Enfin, nous avons montré l'efficacité de notre méthode pour l'élimination de l'oxyde de triphénylphosphine lors d'une réaction de Mitsunobu. La purification d'un milieu réactionnel en SPE au moyen du MIP-Tag a permis l'élimination de 99% de l'oxyde de triphénylphosphine taggé
This work deals with the use of molecular imprinting technology for the design of new tools in organic sythesis. First, we studied the potential of MIPs in organocatalysis through activation in the imprints. For this purpose, several thiourea-cinchona alkaloid derivatives have been prepared so as to be introduced in the polymer cavities. The use of different MIPs synthesised with these polymerisable catalysts in Henry reaction did not show any advantageous effect on reaction rate or enantioselectivity. Secondly, we have prformed the development of a strategy for separation and recovery of a wide range of compounds by relating tag technology with molecular imprinting. Efficiency and selectivity of MIP-Tag for in triazole series have been demonstrated. Tagged tyrosine has been selectively extracted from an amino-acid mixture. Then, the application of this Tag technology for the recovery of pybox and proline catalyst was investigated. Finally, we have demonstrated the efficiency of our process for the removal of triphenylphosphine oxide formed during a Mitsunobu reaction. The removal of 99% of tagged phosphine oxide was perforrmed by the purification of a reaction medium in SPE by means of MIP-Tag
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Thompson, Stephen. "The synthesis of novel DNA-interactive pyrrolo-(2,1-c)[1,4]-benzodiazepin-5-ones." Thesis, University of Liverpool, 2000. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.367072.

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Sallas, Florence. "Méthodologies de fonctionnalisation directe, étude structurale et physico-chimique de nouveaux dérivés de cyclodextrines." Nancy 1, 1996. http://docnum.univ-lorraine.fr/public/SCD_T_1996_0398_SALLAS.pdf.

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Felten, Anne-Sophie. "Synthèse de N-aminopeptides. Application à la synthèse de nouveaux foldamères." Thesis, Vandoeuvre-les-Nancy, INPL, 2007. http://www.theses.fr/2007INPL095N/document.

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Ce travail décrit la synthèse, l’oligomérisation et l’étude structurale de [alpha-N-amino]mères. En extrapolant une stratégie de synthèse originale d’alpha-hydrazinoacides optiquement purs développée au LCPM nous avons pu obtenir de manière satisfaisante les N-aminodipeptides, précurseurs indispensables à la suite du projet. Nous avons pu montrer que l’activation du partenaire acide impliqué dans la réaction clé de Mitsunobu, habituellement obtenue par l’utilisation du groupement phtalimide, pouvait être avantageusement réalisée par l’introduction d’une fonction hydrazone à caractère fortement électroattracteur. Une extension de cette méthode de synthèse sur résine est un résultat qui constitue une mise en œuvre efficace de la réaction de Mitsunobu en SPS. Les N-aminodipeptides obtenus ont ensuite été engagés dans des réactions d’oligomérisation. Une étude préliminaire en phase liquide a permis de démontrer la faisabilité d’un couplage peptidique classique entre deux unités pseudopeptidiques déprotégées. La suite de l’étude a été effectuée sur phase solide et nous a permis d’obtenir les tous premiers oligomères à squelette alpha-N-aminopeptidique jamais synthétisés à ce jour. Enfin, dans le troisième chapitre, ces oligomères ont été étudiés par modélisation moléculaire et par différentes méthodes spectroscopiques (RMN, IR) qui ont permis de mettre en évidence un repliement par l’établissement de liaisons hydrogène intramoléculaires
This work describes the synthesis, the oligomerization and the structural study of N-aminopeptides. By extrapolating an original strategy of hydrazinoacids synthesis developed in the LCPM we were able to obtain N-aminodipeptides in high optical purity in a satisfactory way. These compounds were the indispensable precursors in order to continue the project. We were able to show that the activation of the acidic partner involved in the key reaction of Mitsunobu usually obtained by the use of the phtalimide group, could be advantageously realized by the introduction of a hydrazone moiety with strong electron-withdrawing character. An extension of this method on solid support is a result which constitutes an effective application of a Mitsunobu protocol in Solid Phase Organic Chemistry. The N­aminodipeptides thus obtained were studied in reactions of oligomérisation. A preliminary study in liquid phase allowed to demonstrate that a classic peptidic coupling reaction could occur between two pseudopeptidic units. The continuation of the study was made on solid phase and allowed us to obtain the first [alpha-N-amino]peptides never synthesized to this day. Finally, in the third chapter, these oligomers were studied by molecular modelling and various spectroscopic methods (NMR, IR) who allowed to suggest a folding by the establishment of intramolecular hydrogen bonds
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Fu, Jiasheng. "Investigation of stereoselection by the Mitsunobu reaction and modification of the Hendrickson reaction." Thesis, National Library of Canada = Bibliothèque nationale du Canada, 2000. http://www.collectionscanada.ca/obj/s4/f2/dsk1/tape2/PQDD_0009/NQ59960.pdf.

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Bell, Kathryn Emma. "Advances in the retro-Cope elimination." Thesis, University of Nottingham, 1996. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.307744.

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Books on the topic "Mitsunobu"

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Kanō Mitsunobu no jidai. Tōkyō: Chūō Kōron Bijutsu Shuppan, 2007.

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Tosa Mitsunobu and the small scroll in medieval Japan. Seattle: University of Washington Press, 2009.

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Kenkyūkai, Ōsaka Shakai Jigyōshi, Ōsaka Jikyōkan, and Yao Rinpokan, eds. Yumi wa orezu: Nakamura Mitsunori to Ōsaka no shakai jigyō. Ōsaka-shi: Ōsaka Shakai Jigyōshi Kenkyūkai, 1985.

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Book chapters on the topic "Mitsunobu"

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Laue, Thomas, and Andreas Plagens. "Mitsunobu-Reaktion." In Teubner Studienbücher Chemie, 227–30. Wiesbaden: Vieweg+Teubner Verlag, 1994. http://dx.doi.org/10.1007/978-3-322-94015-5_72.

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Laue, Thomas, and Andreas Plagens. "Mitsunobu-Reaktion." In Teubner Studienbücher Chemie, 228–31. Wiesbaden: Vieweg+Teubner Verlag, 1998. http://dx.doi.org/10.1007/978-3-322-94077-3_73.

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Li, Jie Jack. "Mitsunobu reaction." In Name Reactions, 265. Berlin, Heidelberg: Springer Berlin Heidelberg, 2003. http://dx.doi.org/10.1007/978-3-662-05336-2_198.

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Laue, Thomas, and Andreas Plagens. "Mitsunobu-Reaktion." In Teubner Studienbücher Chemie, 227–30. Wiesbaden: Vieweg+Teubner Verlag, 1994. http://dx.doi.org/10.1007/978-3-322-94726-0_72.

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Li, Jie Jack. "Mitsunobu reaction." In Name Reactions, 407–8. Cham: Springer International Publishing, 2014. http://dx.doi.org/10.1007/978-3-319-03979-4_178.

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Li, Jie Jack. "Mitsunobu reaction." In Name Reactions, 238. Berlin, Heidelberg: Springer Berlin Heidelberg, 2002. http://dx.doi.org/10.1007/978-3-662-04835-1_187.

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Li, Jie Jack. "Mitsunobu reaction." In Name Reactions, 365–67. Berlin, Heidelberg: Springer Berlin Heidelberg, 2009. http://dx.doi.org/10.1007/978-3-642-01053-8_165.

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Li, Jie Jack. "Mitsunobu Reaction." In Name Reactions, 358–61. Cham: Springer International Publishing, 2021. http://dx.doi.org/10.1007/978-3-030-50865-4_96.

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Wang, Fengjiang, and James R. Hauske. "Solid-Phase Synthesis of Benzoxazoles via Mitsunobu Reaction." In Solid-Phase Organic Syntheses, 73–84. New York, USA: John Wiley & Sons, Inc., 2001. http://dx.doi.org/10.1002/0471220434.ch7.

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Taniguchi, Tsuyoshi. "Mitsunobu Reactions in Medicinal Chemistry and Development of Practical Modifications." In Methods in Pharmacology and Toxicology, 97–122. New York, NY: Springer New York, 2021. http://dx.doi.org/10.1007/978-1-0716-1579-9_3.

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Conference papers on the topic "Mitsunobu"

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Kozłowska, Mariola, and Zygmunt Kazimierczuk. "Synthesis of 2'-deoxyribonucleosides by the Mitsunobu reaction." In XIIIth Symposium on Chemistry of Nucleic Acid Components. Prague: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 2005. http://dx.doi.org/10.1135/css200507405.

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Julien Poupart, Julien Poupart, and William D. Lubell William D. Lubell. "Mitsunobu Reaction on Solid Support for Peptide N-terminal Farnesylation." In The 24th American Peptide Symposium. Prompt Scientific Publishing, 2015. http://dx.doi.org/10.17952/24aps.2015.094.

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