Academic literature on the topic 'Julia olefination'

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Journal articles on the topic "Julia olefination"

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Gueyrard, David. "Extension of the Modified Julia Olefination on Carboxylic Acid Derivatives: Scope and Applications." Synlett 29, no. 01 (October 16, 2017): 34–45. http://dx.doi.org/10.1055/s-0036-1590916.

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This account relates our work in the field of modified Julia olefination to extend this very useful olefination method to carboxylic acid derivatives. Since our preliminary results on lactones in 2005, the reaction has been extended to a large range of derivatives (lactams, imides and anhydrides) through an intra- or intermolecular process leading to a great variety of structures (enol ethers, enamides and exo enol esters). This article will also focus on the application of this methodology for the preparation of biologically interesting compounds and/or total syntheses of natural products such as C-disaccharide, bistramide A, jaspine B and maculalactone B.1 Introduction2 Modified Julia Olefination on Lactones2.1 Methylene Enol Ether Synthesis2.2 Substituted Enol Ether Synthesis2.3 Monofluorinated Enol Ether Synthesis2.4 Difluorinated Enol Ether Synthesis3 Applications3.1 Spiroketal Synthesis3.2 Spirocompound Synthesis3.3 Pseudodisaccharide Synthesis3.4 Total Synthesis of Jaspine B4 Modified Julia Olefination on Other Carboxylic Acid Derivatives4.1 Lactam Olefination and Spiroaminal Synthesis4.2 Bicyclic Enamide Synthesis by Intramolecular Modified Julia Olefination on Imides4.3 Modified Julia Olefination on Anhydrides5 Conclusion
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Pfund, Emmanuel, Thierry Lequeux, and David Gueyrard. "Synthesis of Fluorinated and Trifluoromethyl-Substituted Alkenes through the Modified Julia Olefination: An Update." Synthesis 47, no. 11 (April 16, 2015): 1534–46. http://dx.doi.org/10.1055/s-0034-1380548.

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The modified Julia olefination is now a powerful tool for the synthesis of a large range of functionalized alkenes. This short review covers the last five years and provides an overview of the synthesis of mono-, difluoro-, and trifluoromethyl-substituted alkenes via the modified Julia olefination focusing on the novel scope of this reaction.1 Introduction2 Monofluoroalkenes2.1 Disubstituted α- and β-Monofluoroalkenes2.2 Bis(trifluoromethyl)phenyl Sulfones2.3 Conjugated Monofluoroalkenes2.4 Intramolecular Julia Olefination2.5 Smiles Rearrangement from Fluorinated Keto Sulfones2.6 Fluoroallylamines2.7 Fluorinated exo-Glycals2.8 Monofluoroalkenes with an α-Stereocenter at the Allylic Position3 1,1-Difluoroalkenes4 Trifluoromethyl-Substituted Alkenes5 Conclusion
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Kumar, Jayprakash Narayan, and Biswanath Das. "Enantioselective first total synthesis of eujavanoic acid B through organocatalyzed IMDA reaction." RSC Advances 5, no. 19 (2015): 14465–69. http://dx.doi.org/10.1039/c4ra16136j.

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The first total synthesis of the polyketide eujavanoic acid B has been accomplished using 1,3-propane diol as the starting material and involving Maruoka asymmetric allylation, Julia olefination, HWE olefination and organocatalyzed IMDA reaction as the key steps.
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Peddikotla, Prabhakar, Amar G. Chittiboyina, and Ikhlas A. Khan. "Synthesis of Pterostilbene by Julia Olefination." Synthetic Communications 43, no. 23 (September 4, 2013): 3217–23. http://dx.doi.org/10.1080/00397911.2013.775308.

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Yao, Chuan-Zhi, Qiang-Qiang Li, Mei-Mei Wang, Xiao-Shan Ning, and Yan-Biao Kang. "(E)-Specific direct Julia-olefination of aryl alcohols without extra reducing agents promoted by bases." Chemical Communications 51, no. 36 (2015): 7729–32. http://dx.doi.org/10.1039/c5cc01965f.

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Uraguchi, Daisuke, Shinji Nakamura, Hitoshi Sasaki, Yuki Konakade, and Takashi Ooi. "Enantioselective formal α-allylation of nitroalkanes through a chiral iminophosphorane-catalyzed Michael reaction–Julia–Kocienski olefination sequence." Chem. Commun. 50, no. 26 (2014): 3491–93. http://dx.doi.org/10.1039/c3cc49477b.

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Řehová, Lucie, Martin Dračínský, and Ullrich Jahn. "A general approach to iridoids by applying a new Julia olefination and a tandem anion-radical-carbocation crossover reaction." Organic & Biomolecular Chemistry 14, no. 40 (2016): 9612–21. http://dx.doi.org/10.1039/c6ob01599a.

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Zajc, Barbara, and Rakesh Kumar. "Synthesis of Fluoroolefins via Julia-Kocienski Olefination." Synthesis 2010, no. 11 (May 18, 2010): 1822–36. http://dx.doi.org/10.1055/s-0029-1218789.

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Lebrun, Marie-Eve, Paul Le Marquand, and Carl Berthelette. "Stereoselective Synthesis ofZAlkenyl Halides via Julia Olefination." Journal of Organic Chemistry 71, no. 5 (March 2006): 2009–13. http://dx.doi.org/10.1021/jo052370h.

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Mandal, Samir, Apurba Sarkar, Puskin Chakraborty, and Ashoke Chattopadhyay. "Synthetic Studies Towards the Synthesis of 6-Substituted 3-Fluoro-5,6-dihydropyran-2-ones." Synlett 29, no. 01 (August 17, 2017): 75–78. http://dx.doi.org/10.1055/s-0036-1588534.

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Dissertations / Theses on the topic "Julia olefination"

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Blakemore, Paul Richard. "Development and application of the one-pot Julia olefination." Thesis, University of Glasgow, 1999. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.284730.

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Gold, J. B. "Development of a dithiane-Julia olefination reaction : towards the synthesis of callipeltoside A." Thesis, University of Cambridge, 2008. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.599468.

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This doctoral thesis is divided into three sections: Part A, Part B and Part C. Part A is subdivided further into three chapters. In the first of these, an overview of the Julia olefination reaction process as well as its variants is provided, followed by a short description of the application of dithiane methodology in natural product synthesis. The second chapter describes the development of a new methodology based on Julia olefination of substrates derived from dithiane and dithiolane sulfones. Summary and conclusions then follow in chapter three. Part B of this thesis is also subdivided into three sections. The first chapter focuses on the discovery of the callipeltoside natural product family and in this context, structure elucidation and previous total syntheses of callipeltoside A are described. The second chapter outlines the successful synthesis of gram quantities of the crucial aldehyde fragment for the Ley group callipeltoside A synthesis using the double addition of dithiols to ynones developed within the group. Then a preliminary study of the coupling of this key intermediate with a diverse range of vinyl iodide fragments en route to callipeltoside A is described. Full summary, conclusions and details of future work towards completion of the synthesis of calipeltoside A are provided in the third chapter. Finally, a detailed description of experimental procedures and full analytical characterisation data are provided in Part C of this thesis.
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Bedore, Matthew William. "Synthesis of Key Fragments Contained in the Framework of Amphidinol 3." The Ohio State University, 2008. http://rave.ohiolink.edu/etdc/view?acc_num=osu1211485773.

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Shuter, Emily Clare. "Studies toward the synthesis of the microsclerodermin natural products." Faculty of Science, School of Chemistry, University of Sydney, 2006. http://hdl.handle.net/2123/1970.

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Doctor of Philosophy (PhD), Science
A concise stereo-selective synthesis of a protected form of APTO 1, an unusual amino acid component of microsclerodermin C 2, was undertaken. Sequential Sharpless Asymmetric Aminohydroxylation (AA) and Asymmetric Dihydroxylation (AD) reactions were used to introduce the chiral amino and hydroxyl groups. Specific directing groups were chosen to ensure high regio- and enantio-selectivity in these reactions. The target compound was reached in a linear reaction sequence of fourteen steps. The strategy was designed to generate common intermediates which could be used to access analogous amino acid fragments in other microsclerodermins. A protected form of AETD 3, from microsclerodermin E, was synthesised via a late-stage common intermediate. Initial studies into the modification of the sequence to allow access to AMPTD 4 and 10-methyl AMPTD 5 were made.
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Shuter, Emily Clare. "Studies toward the synthesis of the microsclerodermin natural products." Thesis, The University of Sydney, 2005. http://hdl.handle.net/2123/1970.

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A concise stereo-selective synthesis of a protected form of APTO 1, an unusual amino acid component of microsclerodermin C 2, was undertaken. Sequential Sharpless Asymmetric Aminohydroxylation (AA) and Asymmetric Dihydroxylation (AD) reactions were used to introduce the chiral amino and hydroxyl groups. Specific directing groups were chosen to ensure high regio- and enantio-selectivity in these reactions. The target compound was reached in a linear reaction sequence of fourteen steps. The strategy was designed to generate common intermediates which could be used to access analogous amino acid fragments in other microsclerodermins. A protected form of AETD 3, from microsclerodermin E, was synthesised via a late-stage common intermediate. Initial studies into the modification of the sequence to allow access to AMPTD 4 and 10-methyl AMPTD 5 were made.
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Chang, Yan-Ren, and 張延任. "Studies on a Novel Safety-Catch Linker Cleaved by Modified Julia Olefination." Thesis, 2006. http://ndltd.ncl.edu.tw/handle/04437181883842436706.

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碩士
國立中央大學
化學研究所
94
We have known many natural product with double bone maybe have bio-activity in natural world. In order to develop a method of synthesizing quickly various compounds with double bond in organic chemistry. We think the combinatorial chemistry is very good tools in our study. Now We also have known safety-catch linker playing a important role in solid phase. A useful safety-catch linker must have many advantages in synthesis process include easy to take, low cost, stable in any condition and so on. That is a key point we develop a novel safety-catch linker to use in solid phase chemistry. Our safety-catch linker have made a various kinds of alkene because it made double bone in the end of synthesis. We also try our best to study how to control the E-Z form selectivity by base, solvent, Lewis acid and aldehyde. We did not to control the selectivity but have a interesting result. These results will make us more clear and know more detail of the transformation in reaction process. I believe we will succeed in this study.
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Chen, Yeng-Nan, and 陳彥男. "Construction of alpha-GalCer Library via Fluorous Chemistry and Julia-Kociensky Olefination." Thesis, 2011. http://ndltd.ncl.edu.tw/handle/64808149216913853644.

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博士
國立清華大學
化學系
99
Alpha-galactosyl ceramide (alpha-GalCer) has been known to bind to the CD1d receptor on dendritic cells and activate invariant natural killer T (iNKT) cells, which subsequently secrete T-helper-cell 1 (Th1) and Th2 cytokines, which correlate with anti-infection activity and the prevention of autoimmune diseases, respectively. alpha-GalCer elicits the secretion of these two cytokines nonselectively, and thus, its effectiveness is limited by the opposing effects of the Th1 and Th2 cytokines. Therefore there were many alpha-GalCer derivatives syntheized by different strategy for specific releasing Th1 or Th2 cytokines by immune respone, but ultimately no effective approach could construct ??GalCer library for rapid screening. Herein we provided a effectively method to construction of the ??GalCer analogues via Julia-Kociensky olefination induced various lipid chains and coupling reaction connected with various fatty acids and it can be purified effectively by reusable Ftag. This strategy reduced the waste of organic solvent (elute with methanol/water during FSPE) in accordance the concept of green chemistry. The core building block 77 was obtained in 4.9% yield from commerically available D-lyxose and we successfully obtained 65 alpha-GalCer analogues contained 98a (KRN7000) by using this approach. The activity of these compounds will be carried out in the future.
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Book chapters on the topic "Julia olefination"

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Li, Jie Jack. "Julia-Lythgoe olefination." In Name Reactions, 209–10. Berlin, Heidelberg: Springer Berlin Heidelberg, 2003. http://dx.doi.org/10.1007/978-3-662-05336-2_155.

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Li, Jie Jack. "Julia–Kocienski olefination." In Name Reactions, 338–39. Cham: Springer International Publishing, 2014. http://dx.doi.org/10.1007/978-3-319-03979-4_144.

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Li, Jie Jack. "Julia–Lythgoe olefination." In Name Reactions, 340–41. Cham: Springer International Publishing, 2014. http://dx.doi.org/10.1007/978-3-319-03979-4_145.

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Li, Jie Jack. "Julia-Lythgoe olefination." In Name Reactions, 185. Berlin, Heidelberg: Springer Berlin Heidelberg, 2002. http://dx.doi.org/10.1007/978-3-662-04835-1_145.

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Li, Jie Jack. "Julia–Kocienski olefination." In Name Reactions, 309–10. Berlin, Heidelberg: Springer Berlin Heidelberg, 2009. http://dx.doi.org/10.1007/978-3-642-01053-8_135.

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Li, Jie Jack. "Julia–Lythgoe olefination." In Name Reactions, 311–12. Berlin, Heidelberg: Springer Berlin Heidelberg, 2009. http://dx.doi.org/10.1007/978-3-642-01053-8_136.

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Li, Jie Jack. "Julia–Kocienski Olefination." In Name Reactions, 288–90. Cham: Springer International Publishing, 2021. http://dx.doi.org/10.1007/978-3-030-50865-4_75.

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Li, Jie Jack. "Julia–Lythgoe Olefination." In Name Reactions, 291–93. Cham: Springer International Publishing, 2021. http://dx.doi.org/10.1007/978-3-030-50865-4_76.

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Plesniak, Krzysztof, Andrzej Zarecki, and Jerzy Wicha. "The Smiles Rearrangement and the Julia–Kocienski Olefination Reaction." In Topics in Current Chemistry, 163–250. Berlin, Heidelberg: Springer Berlin Heidelberg, 2006. http://dx.doi.org/10.1007/128_049.

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Taber, Douglass F. "Stereocontrolled Construction of Arrays of Stereogenic Centers: The Mullins Synthesis of (-)-Lasiol." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0045.

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Hisashi Yamamoto of the University of Chicago devised (J. Am. Chem. Soc. 2010, 132, 7878) catalyst systems for the enantioselective epoxidation of a Z -homoallylic alcohol 1. Michael J. Krische of the University of Texas developed (J. Am. Chem. Soc. 2010, 132, 1760) a catalyst system for the highly stereoselective addition of the vinyl acetal 5 to an aldehyde 4. Joëlle Prunet of the University of Glasgow showed (Tetrahedron Lett. 2010, 51, 256) that the tandem cyclization/Julia olefination from 7 also proceeded with high stereocontrol. Professor Yamamoto established (J. Am. Chem. Soc. 2010, 132, 5354) that depending on conditions, the aldol condensation of 10 could be directed selectively toward either diastereomer of the product 12. James M. Takacs of the University of Nebraska effected (J. Am. Chem. Soc. 2010, 132, 1740) the enantioselective hydroboration of 10. The other geometric isomer of 10 gave the alternative diastereomer of 12, also with high ee. John Limanto and Shane W. Krska of Merck Process optimized (Organic Lett . 2010, 12, 512) the dynamic kinetic reduction of 13 , giving 14 with excellent diastereocontrol. Professor Krische extended (J. Am. Chem. Soc. 2010, 132, 4562) his reductive homologation to the (racemic) carbonate 15, delivering 16 with excellent dr and ee. Hirokazu Urabe of the Tokyo Institute of Technology showed (Organic Lett. 2010, 12, 1012) that a Grignard reagent under iron catalysis opened the epoxide 17, readily available by Jørgensen-Cordova epoxidation followed by homologation, with clean inversion and high regiocontrol. Fraser F. Fleming of Duquesne University developed (Organic Lett. 2010, 12, 3030) a general route to quaternary alkylated centers by alkylation of nitriles such as 19. Shigeki Matsunaga and Masakatsu Shibasaki of the University of Tokyo devised (J. Am. Chem. Soc. 2010, 132, 3666) a Ni catalyst for the stereoselective conjugate addition of the lactam 22 to a nitroalkene 21. Aldehydes can also be added to nitroalkenes with high dr and ee, as illustrated by the conversion of 24 to 26 reported (J. Am. Chem. Soc. 2010, 132, 50) by Bukuo Ni of Texas A&M University, Commerce.
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