Relevant bibliographies by topics / Mitsunobu reaction

Academic literature on the topic 'Mitsunobu reaction'

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Published: 4 June 2021
Last updated: 25 May 2024

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Journal articles on the topic "Mitsunobu reaction"

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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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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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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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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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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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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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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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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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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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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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Dissertations / Theses on the topic "Mitsunobu reaction"

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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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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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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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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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Fairfull-Smith, Kathryn Elizabeth, and n/a. "Synthetic and Mechanistic Investigations of Some Novel Organophosphorus Reagents." Griffith University. School of Science, 2004. http://www4.gu.edu.au:8080/adt-root/public/adt-QGU20040917.081950.

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The alkoxytriphenylphosphonium ion intermediate of the Mitsunobu reaction for the esterification and inversion of configuration of an alcohol can be generated using the Hendrickson reagent, triphenylphosphonium anhydride trifluoromethanesulfonate, 27. While 27 was used in place of the Mitsunobu reagents (triphenylphosphine and a dialkyl azodicarboxylate) for the esterification of primary alcohols, the reaction failed with secondary alcohols such as (-)-menthol giving predominately elimination rather than the desired SN2 displacement. The difference between the two reactions was shown to be related to the more 'ionic' conditions generated when the Hendrickson reagent 27 was employed. An extreme sensitivity of the Mitsunobu reaction to the presence of salts was discussed and may indicate a mechanism involving ion pair clustering. Five-, six- and seven-membered cyclic analogues of the Hendrickson reagent 90-92 were prepared. A kinetic comparison of the cyclic analogues 90-92 revealed that a considerable increase in the rate of esterification could be achieved when the five-membered ring analogue 90 was used in a non-polar solvent such as toluene. Selected acyclic analogues of the Hendrickson reagent 27 possessing tributyl 118, tricyclohexyl 130 and diphenyl-2-pyridyl 137 functionalities were synthesised. However when 118, 130 and 137 were used for the attempted esterification of (-)-menthol, elimination was the major reaction pathway. Diphenyl-2-pyridylphosphonium anhydride triflate 137 was found to be a useful reagent for the synthesis of acyclic dialkyl ethers from primary alcohols. A polymeric version of the five-membered ring analogue 56, prepared by reaction of the polymer-supported 1,2-bis(diphenylphosphinyl)ethane 57 with triflic anhydride, was used for the preparation of simple esters and amides. A new dehydrating agent, polymer-supported triphenylphosphine ditriflate 157, was readily prepared from the oxidised form of commercially available polymer-supported triphenylphosphine and triflic anhydride. A wide range of dehydration-type reactions, such as ester, amide, anhydride, peptide, ether and nitrile formation, were performed in high yield using polymer-supported triphenylphosphine ditriflate 157. The reagent 157 was easily recovered and re-used several times without loss of efficiency. The use of 4-dimethylaminopyridine allowed the esterification of secondary alcohols with 157 to proceed without elimination and gave esters in high yield but with retention of configuration. Both reagents 56 and 157 provide an alternative to the Mitsunobu reaction, where the use of azodicarboxylates and chromatography to remove the phosphine oxide by-product can be avoided. However, the Mitsunobu reaction retains its supremacy for the inversion of configuration of a secondary alcohol. Preliminary investigations on the phosphityation of alcohols via the Hendrickson reagent 27, 1,3-benzodioxole formation using the Mitsunobu reaction and azodicarboxylate alternatives in the Mitsunobu reaction are described.
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Fairfull-Smith, Kathryn Elizabeth. "Synthetic and Mechanistic Investigations of Some Novel Organophosphorus Reagents." Thesis, Griffith University, 2004. http://hdl.handle.net/10072/367534.

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The alkoxytriphenylphosphonium ion intermediate of the Mitsunobu reaction for the esterification and inversion of configuration of an alcohol can be generated using the Hendrickson reagent, triphenylphosphonium anhydride trifluoromethanesulfonate, 27. While 27 was used in place of the Mitsunobu reagents (triphenylphosphine and a dialkyl azodicarboxylate) for the esterification of primary alcohols, the reaction failed with secondary alcohols such as (-)-menthol giving predominately elimination rather than the desired SN2 displacement. The difference between the two reactions was shown to be related to the more 'ionic' conditions generated when the Hendrickson reagent 27 was employed. An extreme sensitivity of the Mitsunobu reaction to the presence of salts was discussed and may indicate a mechanism involving ion pair clustering. Five-, six- and seven-membered cyclic analogues of the Hendrickson reagent 90-92 were prepared. A kinetic comparison of the cyclic analogues 90-92 revealed that a considerable increase in the rate of esterification could be achieved when the five-membered ring analogue 90 was used in a non-polar solvent such as toluene. Selected acyclic analogues of the Hendrickson reagent 27 possessing tributyl 118, tricyclohexyl 130 and diphenyl-2-pyridyl 137 functionalities were synthesised. However when 118, 130 and 137 were used for the attempted esterification of (-)-menthol, elimination was the major reaction pathway. Diphenyl-2-pyridylphosphonium anhydride triflate 137 was found to be a useful reagent for the synthesis of acyclic dialkyl ethers from primary alcohols. A polymeric version of the five-membered ring analogue 56, prepared by reaction of the polymer-supported 1,2-bis(diphenylphosphinyl)ethane 57 with triflic anhydride, was used for the preparation of simple esters and amides. A new dehydrating agent, polymer-supported triphenylphosphine ditriflate 157, was readily prepared from the oxidised form of commercially available polymer-supported triphenylphosphine and triflic anhydride. A wide range of dehydration-type reactions, such as ester, amide, anhydride, peptide, ether and nitrile formation, were performed in high yield using polymer-supported triphenylphosphine ditriflate 157. The reagent 157 was easily recovered and re-used several times without loss of efficiency. The use of 4-dimethylaminopyridine allowed the esterification of secondary alcohols with 157 to proceed without elimination and gave esters in high yield but with retention of configuration. Both reagents 56 and 157 provide an alternative to the Mitsunobu reaction, where the use of azodicarboxylates and chromatography to remove the phosphine oxide by-product can be avoided. However, the Mitsunobu reaction retains its supremacy for the inversion of configuration of a secondary alcohol. Preliminary investigations on the phosphityation of alcohols via the Hendrickson reagent 27, 1,3-benzodioxole formation using the Mitsunobu reaction and azodicarboxylate alternatives in the Mitsunobu reaction are described.
Thesis (PhD Doctorate)
Doctor of Philosophy (PhD)
School of Science
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Woods, Timothy E. "Elucidating the degree of selectivity for NLO surrogate attachment to model compounds and a co-polyimide using the Mitsunobu reaction /." Online version of thesis, 2008. http://hdl.handle.net/1850/7725.

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Azzouz, Rabah. "Pyridinols protégés et leur utilisation en métallation. Synthèse d'indolizidines à partir de la pyridine : synthèse d'indolizidines à partir de la pyridine." Phd thesis, INSA de Rouen, 2008. http://tel.archives-ouvertes.fr/tel-00559656.

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Dans une première partie, la protection des phénols et des pyridinols a été étudiée. Une nouvelle méthode de tetrahydropyranylation a été développée via la réaction de Mitsunobu. Les pyridinols et des phénols ont ainsi été protégés sous forme d'acétal. Cette méthode est sélective d'un phénol vis-à-vis d'un alcool ou d'une amine. La métallation régiosélective des pyridinols 3- et 4- OTHP a été ensuite réalisée. La fonctionnalisation de ces composés, via des réactions successives de métallation et une hydrolyse acide, a permis la synthèse de pyridinols difonctionnalisés "one-pot". Dans le but d'étudier le pouvoir ortho-directeur du groupe O-THP lors de la réaction de métallation, des essais de déprotonations compétitives ont été réalisés avec un pyridinol protégé par un OMe ou une carbamate. Dans une seconde partie, nous avons étudié une synthèse courte et efficace de la (-)-lentiginosine et de ses épimères à partir de la 2-bromopyridine avec de bons rendements. Nous avons synthétisé la (-)-lentiginosine et deux de ses épimères avec de bons rendements. Au cours de cette synthèse, nous avons développé une nouvelle méthodologie de quaternarisation de pyridine via la réaction de Mitsunobu.
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Fang, Fang. "Synthesis of Bicyclic and Tricyclic Analogues of Oxazolidinone." Ohio University / OhioLINK, 2013. http://rave.ohiolink.edu/etdc/view?acc_num=ohiou1357312054.

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Book chapters on the topic "Mitsunobu reaction"

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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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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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Malkinson, John P., and Robert A. Falconer. "Solid-Phase Synthesis of Thio-Linked C-Terminal Glycopeptides via a Mitsunobu Reaction." In Peptides: The Wave of the Future, 506–7. Dordrecht: Springer Netherlands, 2001. http://dx.doi.org/10.1007/978-94-010-0464-0_234.

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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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Griesbeck, A. G., and T. Sokolova. "Mitsunobu Reaction." In Ethers, 1. Georg Thieme Verlag KG, 2008. http://dx.doi.org/10.1055/sos-sd-037-00252.

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"61. Mitsunobu Reaction." In Organic Chemistry: 100 Must-Know Mechanisms, 136–37. De Gruyter, 2020. http://dx.doi.org/10.1515/9783110608373-061.

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Conference papers on the topic "Mitsunobu reaction"

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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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