Relevant bibliographies by topics / Allylic halogenation

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Academic literature on the topic 'Allylic halogenation'

Author: Grafiati
Published: 6 September 2023

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Journal articles on the topic "Allylic halogenation"

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Pal, Rita, Anupama Das, and Narayanaswamy Jayaraman. "One-pot oligosaccharide synthesis: latent-active method of glycosylations and radical halogenation activation of allyl glycosides." Pure and Applied Chemistry 91, no. 9 (September 25, 2019): 1451–70. http://dx.doi.org/10.1515/pac-2019-0306.

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Abstract Chemical glycosylations occupy a central importance to synthesize tailor-made oligo- and polysaccharides of functional importance. Generation of the oxocarbenium ion or the glycosyl cation is the method of choice in order to form the glycosidic bond interconnecting a glycosyl moiety with a glycosyl/aglycosyl moiety. A number of elegant methods have been devised that allow the glycosyl cation formation in a fairly stream-lined manner to a large extent. The latent-active method provides a powerful approach in the protecting group controlled glycosylations. In this context, allyl glycosides have been developed to meet the requirement of latent-active reactivities under appropriate glycosylation conditions. Radical halogenation provides a newer route of activation of allyl glycosides to an activated allylic glycoside. Such an allylic halide activation subjects the glycoside reactive under acid catalysis, leading to the conversion to a glycosyl cation and subsequent glycosylation with a number of acceptors. The complete anomeric selectivity favoring the 1,2-trans-anomeric glycosides points to the possibility of a preferred conformation of the glycosyl cation. This article discusses about advancements in the selectivity of glycosylations, followed by delineating the allylic halogenation of allyl glycoside as a glycosylation method and demonstrates synthesis of a repertoire of di- and trisaccharides, including xylosides, with varied protecting groups.
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Das, Anupama, and Narayanaswamy Jayaraman. "Carbon tetrachloride-free allylic halogenation-mediated glycosylations of allyl glycosides." Organic & Biomolecular Chemistry 19, no. 42 (2021): 9318–25. http://dx.doi.org/10.1039/d1ob01298c.

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A one-pot CCl4-free allylic halide activation of allyl glycosides, followed by glycosylation with acceptors, is conducted in a latent-active manner. PhCF3 as the solvent and TMSOTf/Tf2O as the promoter system are optimal for the reaction.
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Chen, Chao, Jun-Chen Kang, Chen Mao, Jia-Wei Dong, Yu-Yang Xie, Tong-Mei Ding, Yong-Qiang Tu, Zhi-Min Chen, and Shu-Yu Zhang. "Electrochemical halogenation/semi-pinacol rearrangement of allylic alcohols using inorganic halide salt: an eco-friendly route to the synthesis of β-halocarbonyls." Green Chemistry 21, no. 15 (2019): 4014–19. http://dx.doi.org/10.1039/c9gc01152h.

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Easton, Christopher J., Alison J. Edwards, Stephen B. McNabb, Martin C. Merrett, Jenny L. O'Connell, Gregory W. Simpson, Jamie S. Simpson, and Anthony C. Willis. "Allylic halogenation of unsaturated amino acids." Org. Biomol. Chem. 1, no. 14 (2003): 2492–98. http://dx.doi.org/10.1039/b303719c.

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Yin, Jiandong, Christina E. Gallis, and John D. Chisholm. "Tandem Oxidation/Halogenation of Aryl Allylic Alcohols under Moffatt−Swern Conditions." Journal of Organic Chemistry 72, no. 18 (August 2007): 7054–57. http://dx.doi.org/10.1021/jo0711992.

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Hanson, James R., Peter B. Hitchcock, Paul B. Reese, and Almaz Truneh. "Steroidal allylic and homoallylic rearrangements during halogenation with triphenylphosphine and carbon tetrachloride." Journal of the Chemical Society, Perkin Transactions 1, no. 6 (1988): 1469. http://dx.doi.org/10.1039/p19880001469.

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Liu, Na, Casi M. Schienebeck, Michelle D. Collier, and Weiping Tang. "Effect of halogenation reagents on halocyclization and Overman rearrangement of allylic trichloroacetimidates." Tetrahedron Letters 52, no. 47 (November 2011): 6217–19. http://dx.doi.org/10.1016/j.tetlet.2011.09.057.

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Bandgar, Babasaheb P., and Sampada V. Bettigeri. "Efficient and Selective Halogenation of Allylic and Benzylic Alcohols under Mild Conditions." Monatshefte f�r Chemie/Chemical Monthly 135, no. 10 (August 13, 2004): 1251–55. http://dx.doi.org/10.1007/s00706-004-0212-8.

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Hamashima, Yoshitaka, and Yuji Kawato. "Enantioselective Bromocyclization of Allylic Amides Mediated by Phosphorus Catalysis." Synlett 29, no. 10 (May 14, 2018): 1257–71. http://dx.doi.org/10.1055/s-0036-1591579.

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Halocyclization of alkenes is commonly employed to increase molecular complexity during organic synthesis because it enables double installation of heteroatoms on a carbon–carbon double bond. Moreover, stereodefined halogenated compounds are widely found among naturally occurring compounds and can serve as versatile chiral building blocks. Therefore, the development of asymmetric halocyclization reactions is of great interest and, in recent years, there has been remarkable progress in catalytic asymmetric halogenation reactions. This account summarizes recent progress made by our group on phosphorus-­catalyzed enantioselective bromocyclization of allylic amides. Building on a comprehensive study of the reaction mechanism, we discovered an intriguing catalytic reaction in which P+Br species serves as a fine-tuning element for substrate fixation. We also describe the application of this bromocyclization to asymmetric desymmetrization of 1,4-diene substrates and a concise synthesis of the HIV-protease inhibitor ­nelfinavir using the newly developed desymmetrization reaction as a key step.1 Introduction2 Enantioselective Bromocyclization of Allylic Amides with a BINAP Catalyst2.1 Bromocyclization with a P/P Catalyst2.2 Bromocyclization with a P/P=O Catalyst3 Desymmetrization of Bisallylic Amides through Enantioselective Bromocyclization3.1 Desymmetrization of Bisallylic Amides3.2 Enantioselective Synthesis of Nelfinavir4 Summary
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Liu, Na, Casi M. Schienebeck, Michelle D. Collier, and Weiping Tang. "ChemInform Abstract: Effect of Halogenation Reagents on Halocyclization and Overman Rearrangement of Allylic Trichloroacetimidates." ChemInform 43, no. 9 (February 2, 2012): no. http://dx.doi.org/10.1002/chin.201209054.

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Dissertations / Theses on the topic "Allylic halogenation"

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Legoupy, Stéphanie. "Synthèse et réactivité de nouveaux complexes organométalliques chiraux du rhénium." Rennes 1, 1997. http://www.theses.fr/1997REN10148.

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Le travail présenté dans ce mémoire concerne la synthèse et la réactivité de complexes du rhénium. De nouveaux complexes organométalliques chiraux du rhénium des alcools propargyliques et homoallylique ont été synthétisés. Des alcools allyliques secondaires et 1,2-disubstitues ont été coordonnés à l'entité chirale (#5C#5H#5)Re(No)(Pph#3)#+Bf#4#-. Dans le cas du 3-buten-2-ol complexe, les deux diastéréoisomères ont pu été séparés. L'étude de la réactivité de ces complexes du rhénium a montré qu'ils sont compatibles avec des réactions d'oxydation, de Wittig, de réduction, d'estérification, de chloration, de bromation et de fluoration. L'entité organométallique (#5C#5H#5)Re(No)(Pph#3)#+Bf#4#- s'est montrée un bon groupement protecteur d'une seule double liaison au cours de ces réactions. Les substitutions allyliques, catalysées par un acide de Lewis, sur les complexes du rhénium des alcools allyiques ont été étudiées. Quelque soit le nucléophile, ces réactions sont régio- et stéréosélectives et se font avec rétention de configuration. Un mécanisme impliquant un complexe -allyl dicationique du rhénium a été proposé. Le rôle activateur du rhénium a été mis en évidence.
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Das, Anupama. "Allylic Halogenation Route to Latent-Active Trans-Glycosylation of Allyl Glycoside Donors." Thesis, 2021. https://etd.iisc.ac.in/handle/2005/5626.

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Allylic halogenation of allyl glycosides as a new route to allyl glycoside donors in glycosylations is investigated in this thesis. Allyl functionality is one of the commonly adopted protecting groups to hydroxyl groups in sugar chemistry. In addition, allyl glycosides act as glycosyl donors, through isomerization to the corresponding vinyl glycosides. Facile conversion of allyl moiety to other functionalities, as well as, stabilities under acidic and basic conditions offer rich possibilities of this moiety in sugar chemistry. Chapter 1 provides a succinct overview of glycosylation reactions and mechanisms. An area of intense interest is to transform a latent allyl moiety to an active glycosyl donor. In this effort, allylic halogenation reaction is considered appealing, due to the expected reactivity of the mixed halo-acetal of allyl glycoside towards an electrophile and the subsequent transformation to a glycosylation-active intermediate, suitable as an active glycosyl donor. Early experiments show that allylic bromination of allyl glycosides, using N-bromosuccinimide (NBS)/azo-bis-isobutyronitrile (AIBN) in CCl4 generates mixed halo-allyl glycoside intermediate, the reaction of which with an acceptor in the presence of Ag(I) or triflic acid (TfOH) affords the corresponding trans-glycoside in a good yield. The reaction is verified with a number of glycoside acceptors, including allyl glycoside acceptors. In the case of allyl glycoside acceptors, the resulting trans-glycoside possesses allyl moiety at the reducing end, which, in turn, is subjected allylic activation and subsequent glycosylation. Di-, tri- and tetrasaccharide syntheses are accomplished in good yields by this new route. Chapter 2 describes the development of this new method. Radical halogenations in CCl4 warranted a replacement to the solvent, as well as, further optimizations of the reaction. In these efforts, diethylcarbonate (Et2O)2CO) is identified as a suitable solvent to conduct (i) radical halogenation and (ii) the subsequent glycosylation. The glycosylation is promoted either by TfOH or trimethylsilyl triflate (TMSOTf). A one-pot methodology is developed and method is verified with the synthesis of xyloyranoside, mono-, di- and trisaccharides. Chapter 3 provides the details of these developments. Halo-allyl mixed acetal of allyl glycoside is found to undergo S¬N2 and S¬¬¬¬N2’ reactions with thiolate nucleophiles. The SN2’ reaction leads to 3-thiocresylpropenyl (TCP) glycoside, as a stable vinyl glycoside, which can be stored for longer duration, unlike, vinyl glycosides that are quite unstable due to faster hydrolysis. TCP glycoside is subjected to remote activation using iodonium reagent and activation leads to the formation of glycosylation active intermediate. Glycosylations with aglycosyl and glycosyl acceptors are conducted facile and the corresponding trans-glycosides are obtained in excellent yields. Chapter 4 describes the development of this new, stable TCP-based vinyl glycoside methodology in glycosylations. Overall, the thesis illustrates establishing allyl glycosides as glycosyl donors as allylic halogenations and subsequent glycosylations. The new method merits in the repertoire of contemporary glycosylation techniques of remote activation-based glycosylations.
UGC
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Book chapters on the topic "Allylic halogenation"

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Taber, Douglass F. "C–C Bond Construction: The Zhu Synthesis of Goniomitine." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0023.

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Non-enolizable β-keto esters such as 3 are fragile and difficult to prepare. Karl J. Hale of Queen’s University Belfast devised (Org. Lett. 2013, 15, 370) soft enolization con­ditions for methoxycarbonylation of 1 with 2. Zheng Huang of the Shanghai Institute of Organic Chemistry coupled (Org. Lett. 2013, 15, 1144) 4 with 5 under Ir catalysis to make 6. Tomoya Miura and Masahiro Murakami of Kyoto University combined (Angew. Chem. Int. Ed. 2013, 52, 3883) the diazo precursor 8 with the allylic alco­hol 7 to give 9, the product of Claisen rearrangement. Tsuyoshi Satoh of the Tokyo University of Science showed (Tetrahedron Lett. 2013, 54, 2533) that the combina­tion of the carbenoid 10 with a ketone enolate 11 led to the cyclopropanol (not illus­trated). Jin Kun Cha of Wayne State University found (Org. Lett. 2013, 15, 1780) that such cyclopropanols coupled with an acid chloride 12 under Pd catalysis to give the diketone 13. Christopher J. O’Brien of Dublin City University established (Chem. Eur. J. 2013, 19, 5854) conditions for the catalytic Wittig reaction of 14 with 15 to give 16, with in situ reduction of the phosphine oxide. Amir H. Hoveyda of Boston College showed (Org. Lett. 2013, 15, 1414) that the allene of 17 underwent selective borylation, lead­ing after coupling with 18 to the triene 19. Damian W. Young of the Broad Institute demonstrated (Org. Lett. 2013, 15, 1218) that ring-closing metathesis gave the alkenyl silane 20 with high geometric control. Halogenation to give 21 could then proceed with either retention or inversion of alkene geometry. Jianwei Sun of the Hong Kong University of Science and Technology and Zigang Li of the Shenzen Graduate School of Peking University condensed (J. Am. Chem. Soc. 2013, 135, 4680) the alkyne 22 with 23 to give the trisubstituted alkene 24 with high geometric control. The condensation worked equally well with medium and large ring ethers. Hua-Jian Xu of the Hefei University of Technology combined (Org. Lett. 2013, 15, 1472) the bromo alkyne 25 with the carboxylate 26 to give the nitrile 27.
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Taber, Douglass. "Construction of Alkenes, Alkynes and Allenes." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0020.

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Products such as 3 and 6 are usually prepared by phosphonate condensation. J. S. Yadav of the Indian Institute of Technology, Hyderabad found (Tetrahedron Lett. 2008, 49, 4498) that the cation-exchange resin Amberlyst-15 in CH2Cl2 mediated the condensation of a terminal alkyne such as 1 with an aldehyde to give the enone 3. Similarly, Teruaki Mukaiyama of Kitasato University showed (Chemistry Lett. 2008, 37, 704) that tetrabutylammonium acetate mediated the condensation of 5 with an aldehyde such as 4 to give the ester 6. David M. Hodgson of the University of Oxford described (J. Am. Chem. Soc. 2008, 130, 16500) the optimization of the Schlosser protocol for the condensation of a phosphorane with an aldehyde 7 followed by deprotonation and halogenation, to deliver the alkenyl halide 9 with good geometric control. Jun Terao of Kyoyo University and Nobuaki Kambe of Osaka University accomplished (Chem. Commun. 2008, 5836) the homologation of a halide such as 10 to the corresponding allylic Grignard reagent 12. Primary, secondary and tertiary halides worked well. Jennifer Love of the University of British Columbia developed (Organic Lett. 2008, 10, 3941) a Rh catalyst for the addition of thiols to terminal alkynes such as 13, and found that the product thioether 14 coupled smoothly with Grignard reagents to deliver the 1,1-disubstituted alkene 15. Glenn C. Micalizio, now at Scripps Florida, established (J. Am. Chem. Soc. 2008, 130, 16870) what appears to be a general method for the construction of Z-trisubstituted alkenes such as 18. The Ohira protocol has become the method of choice for converting an aldehyde 19 to the alkyne 21. We have found (Tetrahedron Lett. 2008, 49, 6904) that the reagent 20 offers advantages in price, preparation and handling. Bo Xu and Gerald B. Hammond of the University of Louisville observed (Organic Lett. 2008, 10, 3713) that an allene ester such as 22 is readily homologated to the alkyne 23. Ashton C. Partridge of Massey University extended (Tetrahedron Lett. 2008, 49, 5632) condensation with the aryl phosphonate 25 to porphyrin aldehydes, leading to alkynes such as 26.
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Taber, Douglass. "Reactions of Alkenes." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0022.

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One of the most powerful of alkene transformations is enantioselective epoxidation. Tsutomu Katsuki of Kyushu University has developed (Angew. Chem. Int. Ed. 2007, 46, 4559) a Ti catalyst that with H2O2, selectively epoxidized terminal alkenes with high ee. The same catalyst converted a Z 2-alkene such as 3 into the epoxide. This is significant, because such epoxides are opened with nucleophiles selectively at the less congested center. Novel procedures for alkene functionalization have been put forward. Philippe Renaud of the University of Berne has developed (Adv. Synth. Cat. 2008, 350, 1163) a simple protocol for terminal halogenation, based on catalyzed addition of catecholborane, followed by free radical substitution. Sulfides and selenides were also prepared. H. Zoghlami of the Faculty of Sciences of Tunis has devised (Tetrahedron Lett. 2007, 48, 5645) an oxidative sulfinylation, converting a terminal alkene 7 to the sulfide 8. M. Christina White of the University of Illinois (J. Am. Chem. Soc. 2008, 130, 3316) and Guosheng Liu of the Shanghai Institute of Organic Chemistry (Angew. Chem. Int. Ed. 2008, 47, 4733) independently developed Pd catalysts for the oxidation of a terminal alkene 9 to the terminal allylic amine 10. Shannon S. Stahl of the University of Wisconsin-Madison has established (Organic Lett. 2007, 9, 4331) conditions for the complementary transformation of a terminal alkene 11 to the enamide 12. Douglas B. Grotjahn of San Diego State University has optimized (J. Am. Chem. Soc. 2007, 129, 9592) Ru-catalyzed alkene (“zipper”) migration, effecting the conversion of 13 to 14 and of 15 to 16 . There have been several new observations on alkene cleavage. Marcus A. Tius of the University of Hawaii and Bakthan Singaram of the University of California, Santa Cruz have found (Tetrahedron Lett. 2008, 49, 2764) that epoxides such as 17 are cleaved directly by NaIO4, providing a simple alternative to ozonolysis. Rolando A. Spanevello of the Universidad Nacional de Rosario has extended (Tetrahedron 2007, 63, 11410) unsymmetrical ozonolysis to highly substituted norbornene derivatives such as 19, observing 20 as the only product. Patrick H. Dussault of the University of Nebraska–Lincoln has established (J. Org. Chem. 2008, 73, 4688) that alkene ozonolysis in wet acetone delivered the ketone or aldehyde directly, without reductive workup.
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Taber, Douglass. "Preparation of Benzene Derivatives: The Barrett Syntheses of Dehydroaltenuene B and 15G256β." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0064.

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Several new methods for the direct functionalization of Ar-H have appeared. Hisao Yoshida of Nagoya University observed (Chem. Comm. 2008, 4634) that under irradiation, TiO2 in water effected meta hydroxylation of benzonitrile 1 to give the phenol 2. Anisole showed ortho selectivity, while halo and alkyl aromatics gave mixtures. Melanie S. Sanford of the University of Michigan reported (J. Am. Chem. Soc. 2008, 130, 13285) a complementary study of Pd-catalyzed ortho acetoxylation. Jin-Quan Yu of Scripps/La Jolla developed (Angew. Chem. Int. Ed. 2008, 47, 5215) a Pd-catalyzed protocol for ortho halogenation of aromatic carboxylates such as 3. A related protocol (J. Am. Chem. Soc. 2008, 130, 17676) led to ortho arylation. Trond Vidar Hansen of the University of Oslo devised (Tetrahedron Lett. 2008, 49, 4443) a one-pot procedure for the net ortho cyanation of phenols such as 5 to the salicylnitrile 6. Robin B. Bedford of the University of Bristol, Andrew J. M. Caffyn of the University of the West Indies and Sanjiv Prashar of the Universidad Rey Juan Carlos established (Chem. Comm. 2008, 990) a Rh-catalyzed protocol for ortho arylation of phenols such as 7. Laurent Désaubry of the Université Louis Pasteur observed (Tetrahedron Lett. 2008, 49, 4588) regioselective coupling of unsymmetrical difluorobenzenes such as 9 to give the ether 10. Fuk Yee Kwong of Hong Kong Polytechnic University extended (Angew. Chem. Int. Ed. 2008, 47, 6402) Pd-mediated amination to the notoriously difficult mesylates, such as 11. John F. Hartwig of the University of Illinois reported (J. Am. Chem. Soc. 2008, 130, 13848) a related method for the amination of aryl tosylates. Hong Liu of the Shanghai Institute of Materia Medica found (Organic Lett. 2008, 10, 4513) that the Fe-catalyzed amination of aryl halides such as 13 sometimes gave mixtures of regioisomers. Hideki Yorimitsu and Koichiro Oshima of Kyoto University effected (Angew. Chem. Int. Ed. 2008, 47, 5833) Ag-catalyzed Grignard cross coupling with aryl halides, converting 15 into 16. Note that silyl aromatics such as 16 are readily reduced under dissolving metal conditions to give allyl silanes.
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