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Relevant bibliographies by topics / Lithium amides

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Academic literature on the topic 'Lithium amides'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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Journal articles on the topic "Lithium amides"

1

Majewski, Marek, Agnieszka Ulaczyk-Lesanko, and Fan Wang. "Chiral lithium amides on polymer support Synthesis and use in deprotonation of ketones." Canadian Journal of Chemistry 84, no. 2 (February 1, 2006): 257–68. http://dx.doi.org/10.1139/v06-006.

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A number of chiral secondary amines attached to Merrifield resin or to noncrosslinked (soluble) polystyrene support were synthesized. The corresponding lithium amides, generated from these amines by treatment with BuLi, react with tropinone, a model symmetrical ketone, to give the corresponding enolates enantioselectively (ee up to 75%). The enolates were trapped either as the corresponding aldol adducts by a reaction with benzaldehyde or as ring-opening products in a reaction with a chloroformate.Key words: chiral lithium amides, polymer-supported reagents, deprotonation, enolates, tropinone.

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Nodzewska, Aneta, Agnieszka Wadolowska, Katarzyna Podgorska, Damian Pawelski, and Ryszard Lazny. "Synthesis of Solid-phase Supported Chiral Amines and Investigation of Stereoselectivity of Aldol Reactions of Amine-free Tropinone Enolate." Current Organic Chemistry 23, no. 17 (November 2, 2019): 1867–79. http://dx.doi.org/10.2174/1385272823666190916145332.

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Seven selected chiral mono-, di-, and tridentate amines supported on insoluble polymer were effectively prepared from corresponding primary amines or secondary amino alcohols and Merrifield resin. The reaction of the polymer-supported amines with excess n-butyllithium gave the corresponding lithium amide bases, which were tested in the aldol reactions of tropinone with benzaldehyde. The deprotonation reactions were carried out with or without separation of the lithium enolate from polymer-supported reagents. Using the procedure with separation of lithium enolate from supported chiral reagent different results were obtained with or without the addition of LiCl despite the fact that aggregate formation of Merrifield resin supported Li-amides is hindered. Without the additive, the aldol products were obtained in low diastereoselectivity and enantioselectivity, whereas the addition of LiCl resulted in a significant increase of de and ee even when LiCl was added after the deprotonation step and separation of the chiral amine.

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3

Bisai, Milan Kumar, Kritika Gour, Tamal Das, Kumar Vanka, and Sakya S. Sen. "Lithium compound catalyzed deoxygenative hydroboration of primary, secondary and tertiary amides." Dalton Transactions 50, no. 7 (2021): 2354–58. http://dx.doi.org/10.1039/d1dt00364j.

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4

Sorokin, Vladimir I., Valery A. Ozeryanskii, Gennady S. Borodkin, Anatoly V. Chernyshev, Max Muir, and Jon Baker. "Preparation of Dialkylamino-Substituted Benzenes and Naphthalenes by Nucleophilic Replacement of Fluorine in the Corresponding Perfluoroaromatic Compounds." Zeitschrift für Naturforschung B 61, no. 5 (May 1, 2006): 615–25. http://dx.doi.org/10.1515/znb-2006-0519.

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The reactions between hexafluorobenzene (HFB) and octafluoronaphthalene (OFN) with secondary aliphatic amines (pyrrolidine, dimethylamine and piperidine) and lithium amides (pyrrolidide, dimethylamide and piperidide) have been investigated both experimentally and (in part) theoretically. With amines HFB, depending on the selected conditions, gives either di-substituted products or a complex mixture of di-, tri- and tetrasubstituted compounds. Under similar conditions OFN produces almost exclusively the 2,3,6,7-tetrasubstituted compound. Interaction of HFB with the more nucleophilic lithium amides results in the replacement of four fluorines giving 1,2,4,5-tetrasubstituted difluorobenzenes, while OFN under similar conditions with lithium pyrrolidide produces an inseparable mixture of 1,2,4,5,6,8-hexa- and 1,2,3,4,5,6,8-hepta-substituted derivatives. With lithium dimethylamide, it is possible to substitute six (in dioxane) or seven (in THF) fluorines in OFN. Lithium piperidide in all employed solvents reacts with OFN to give only the 1,2,4,5,6,8-hexasubstituted derivative. Theoretical calculations indicate that with lithium dimethylamide the third fluorine is substituted at position 1, whereas with dimethylamine it is position 3. The basicities of selected hexaand heptakis(dialkylamino)naphthalenes have been measured; they are all stronger bases than 1,8- bis(dimethylamino)naphthalene, although by less than expected.

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Katritzky, Alan R., Jinlong Jiang, and Philip A. Harris. "Synthesis of α-(arylideneamino)alkylamines." Canadian Journal of Chemistry 69, no. 7 (July 1, 1991): 1153–55. http://dx.doi.org/10.1139/v91-171.

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α-(Arylideneamino)alkylamines 4 are prepared in high yields by the reaction of 1-(benzotriazol-1-yl)-N-triphenylphosphorylidenemethylamine (betmip) 2 with lithium amides and treatment of the resulting intermediates 3 with aryl aldehydes. Key words: benzotriazole, lithium amides, aryl aldehydes.

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6

von Bülow, Rixa, Stephan Deuerlein, Thomas Stey, Regine Herbst-Irmer, Heinz Gornitzka, and Dietmar Stalke. "N-Aryl Anions: Half Way between Amides and Carbanions." Zeitschrift für Naturforschung B 59, no. 11-12 (December 1, 2004): 1471–79. http://dx.doi.org/10.1515/znb-2004-11-1216.

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A ‘carbanion’ can coordinate to a metal like an ‘amide’ if there is a nitrogen atom present to withdraw electron density from the formally negatively charged carbon center. On the other hand, shifting the negative charge from the amido nitrogen atom to the carbon substituent should convert an ‘amidic’ into a ‘carbanionic’ coordination behavior. This seems feasible with various substituents at the aromatic ring in a primary amide. This paper is concerned with the influence of aromatic substitution, as well as with the nature of the metal ion on the coordination mode of an amide ligand. Discussed are the parent lithium anilide [(thf)2LiNH(C6H5)]2 (1), the pentafluorinated lithium anilide [(thf)2LiNH(C6F5)]2 (2) and the lithium amino benzonitrile [(thf)2LiNH(C6H4pCN)]2 (3). All amide ligands coordinate the lithium cation exclusively with their amido nitrogen atom. In the dimeric structure of 1 the atom can be regarded to be sp2-hybridized. Fluorine substitution of the ring results in a slightly more pronounced coupling of the negative charge to the aromatic ring. A para-nitrile group further enhances quinoidal perturbation of the C6-perimeter from six-fold symmetry. Consequently, the ipso- and ortho-carbon atoms of the ring are partially negative charged. Those carbon atoms are only attractive for the soft rubidium cation in an aza allylic coordination in [(thf)2RbNH(C6H4pCN)]n (4) but not to the hard lithium cation.

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7

Majewski, Marek, Ryszard Lazny, and Agnieszka Ulaczyk. "Enantioselective ring opening of tropinone. A new entry into tropane alkaloids." Canadian Journal of Chemistry 75, no. 6 (June 1, 1997): 754–61. http://dx.doi.org/10.1139/v97-091.

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The lithium enolate of tropinone reacts with alkyl chloroformates to give 6-N-carboalkoxy-N-methyl-2-cycloheptenones (4). These compounds can be produced enantioselectively, in up to 95% ee, if chiral lithium amides (derived from optically pure amines 5–7) are used for deprotonation of tropinone in the presence of additives. The effect of additives such as LiCl, LiBr, LiF, LiClO4, CeCl3, ZnCl2, LiOH, TMEDA, HMPA, and DMPU on enantioselectivity of this deprotonation–ring opening sequence varies from slight to very large depending on the chiral amide – additive combination. Especially large increases in enantioselectivity are observed when the chiral, C2 symmetrical, lithium bis-α,α′-methylbenzylamide (Li-5a) is used with one equivalent of LiCl. This reagent is best generated in situ from the corresponding amine hydrochloride and n-BuLi (2 equiv.). The ring-opening reaction combined with transposition of the carbonyl group (via Wharton reaction or allylic oxidation) provides a new method of stereoselective synthesis of tropane alkaloids having a protected hydroxyl at C-6 or C-7 (6β- and 7β-acetoxytropanes 14a, b) and physoperuvine (19). Keywords: enantioselective deprotonation, tropane alkaloids.

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8

de Jong, Jorn, Dorus Heijnen, Hugo Helbert, and Ben L. Feringa. "One-pot, modular approach to functionalized ketones via nucleophilic addition/Buchwald–Hartwig amination strategy." Chemical Communications 55, no. 20 (2019): 2908–11. http://dx.doi.org/10.1039/c8cc08444k.

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9

Majewski, Marek, and Guo-Zhu Zheng. "Stereoselective deprotonation of tropinone and reactions of tropinone lithium enolate." Canadian Journal of Chemistry 70, no. 10 (October 1, 1992): 2618–26. http://dx.doi.org/10.1139/v92-330.

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Tropinone (6) was deprotonated with lithium diisopropylamide and with chiral lithium amides (18–24) and the resulting enolates (two enantiomers) were treated with electrophiles. The aldol reaction with benzaldehyde and deuteration were both diastereoselective. The former yielded only one isomer (exo, anti) of the aldol 8a; the latter proceeded from the exo face. This selectivity permitted us to probe the deprotonation of tropinone with lithium amides; it was concluded that the reaction involves predominantly the exo axial protons. The reaction of tropinone enolate with ethyl chloroformate led, via a ring opening, to the cycloheptenone derivative 9. The reaction with methyl cyanoformate yielded, in the presence of silver acetate and acetic acid, the β-ketoester 8b; however, in the absence of these additives, and especially when 12-crown-4 was added to the enolate, a ring opening leading to the pyrrolidine derivative 10 occurred instead. Deprotonation of tropinone with chiral lithium amides proceeded with modest enantioselectivity. A synthesis of non-racemic anhydroecgonine via this strategy allowed establishing the absolute stereochemistry of deprotonation.

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10

KOGA, Kenji. "Enantioselective reactions using chiral lithium amides." Journal of Synthetic Organic Chemistry, Japan 48, no. 6 (1990): 463–75. http://dx.doi.org/10.5059/yukigoseikyokaishi.48.463.

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Dissertations / Theses on the topic "Lithium amides"

1

Muller, Catherine R. "Lithium amides in synthesis." Thesis, University of Oxford, 2005. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.413176.

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Paul, Jane M. "Chiral lithium amides in asymmetric synthesis." Thesis, University of Surrey, 1994. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.259571.

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Bambridge, Kimberley. "Novel stereoselective applications of homochiral lithium amides." Thesis, University of Nottingham, 1994. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.260995.

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4

Bray, Christopher D. "New reactions of epoxides with hindered lithium amides." Thesis, University of Oxford, 2005. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.526579.

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5

Smyth, G. Darren. "Asymmetric synthesis via #beta#-amino esters." Thesis, University of Oxford, 1996. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.297678.

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6

Prestly, Mark Robert. "Chiral lithium amides : reactivity studies and applications to target synthesis." Thesis, University of Birmingham, 2013. http://etheses.bham.ac.uk//id/eprint/3961/.

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Chiral lithium amide bases allow the desymmetrisation of prochiral substrates and the production of enantiomerically enriched products, which are vital for the pharmaceutical industry and the total synthesis of natural products. Chapter 1 gives a brief review of this area and the progress that has been achieved over the last three decades. In Chapter 2 deprotonation of a ketone and an imide substrate using both chiral and achiral bases is described. Within the development of catalytic chiral lithium amide base methodology, competition reactions (Chapter 3) and lithium exchange experiments (Chapter 4) were carried out between two amine species. It was found that there were appreciable differences in the rate of deprotonation of the substrate between the lithium amides studied. Chapter 5 describes the design and synthesis of new fluorinated chiral diamines which we hoped could be used as effective chiral lithium amide bases in sub-stoichiometric amounts. Initial work was also carried out on the total synthesis of the diterpenoid alkaloid concavine. A chiral lithium amide base was used to introduce asymmetry into the synthetic route and the synthesis of the fused oxazepane ring moiety was completed (Chapter 6).

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7

Lee, James A. "The use of functionalised lithium amides in the total synthesis of alkaloids." Thesis, University of Oxford, 2012. http://ora.ox.ac.uk/objects/uuid:f558ce63-6b8d-4a9f-8f20-8b231d7a110e.

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This thesis is concerned with the application of the conjugate addition of functionalised lithium amides in the asymmetric syntheses of (−)-morphine and all members of the homalium alkaloids. Chapter 1 introduces the conjugate addition reaction as an important bond forming reaction, and explores its utility in the asymmetric synthesis of a variety of natural products. The conjugate addition of secondary lithium amides derived from α-methylbenzylamine is discussed, along with its application to the asymmetric synthesis of alkaloids. Chapter 2 describes two distinct attempts towards the asymmetric synthesis of (−)-morphine, both reliant upon the lithium amide conjugate addition and an intramolecular Diels-Alder reaction to set the five required stereogenic centres. The use of the novel and highly functionalised reagent lithium (R)-N-[2′-(7-methoxybenzofuran-3-yl)ethyl]-N-(α-methylbenzyl)amide and its derivatives is reported. Chapter 3 focuses on the use of the novel reagent lithium (R)-N-(3-chloroprop-1-yl)-N-(α-methylbenzyl)amide and its derivatives in the asymmetric synthesis of two of the homalium alkaloids, (−)-(S,S)-homaline and (−)-(R,R)-hopromine, culminating in the most efficient syntheses of these alkaloids to date. Further, a sample of the (4′R,4′′S)-diastereoisomer of hopromine was synthesised, serving to confirm the proposed absolute configuration within natural (−)-(R,R)-hopromine. Chapter 4 extends the methodology developed in chapter 3 to the asymmetric synthesis of all possible diastereoisomers of the remaining homalium alkaloids, (−)-hopromalinol and (−)-hoprominol. These syntheses were used to propose the absolute configurations within these alkaloids, and therefore represented the first asymmetric syntheses of natural (−)-(4′S,4″R,2‴R)-hopromalinol and (−)-(R,R,R)-hoprominol. Chapter 5 contains full experimental procedures and characterisation data for all compounds synthesised in Chapters 2, 3 and 4.

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8

Misra, M. C. "Some palladium and platinum chemistry involving divalent amides of germanium or tin; and some aspects of lithium amide chemistry." Thesis, University of Sussex, 1986. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.373154.

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9

Scott, Natalie M(Natalie Maree) 1976. "Diverse lanthanoid and lithium complexes with pendant donor amide ligands." Monash University, Dept. of Chemistry, 2001. http://arrow.monash.edu.au/hdl/1959.1/8984.

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10

Kruchinin, Dennis. "Lithium amide mechanisms." Thesis, University of Oxford, 2006. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.437356.

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Books on the topic "Lithium amides"

1

Granander, Johan. Asymmetric synthesis mediated by chiral lithium amides: Design, structure and selectivity. Göteborg: Göteborg University, Faculty of Science, 2005.

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2

Rahman, Shirley Katherine. Preparation and use of chiral lithium amide bases in organic synthesis. Salford: University of Salford, 1988.

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3

Hewitt, Jacqueline Diane. Enantioselective preparation of CIS-Bicyclo [3.3.0] octane derivatives using chiral lithium amide bases. Salford: University of Salford, 1990.

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4

Doquang, Mailan S. The Lithic Garden. Oxford University Press, 2018. http://dx.doi.org/10.1093/oso/9780190631796.001.0001.

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This ambitious book offers new perspectives on the role of vegetal ornament in medieval church design. Focusing on an extensive series of foliate friezes articulating iconic French monuments, such as Cluny III, Amiens Cathedral, and Mont-Saint-Michel, it demonstrates that church builders strategically used organic motifs to integrate the interior and exterior of their structures, and to reinforce the connections and distinctions between the entirety of the sacred edifice and the profane world beyond its boundaries. Mailan S. Doquang shows that, contrary to widespread belief, monumental flora was not just an extravagant embellishment devoid of meaning and purpose, or an epiphenomenon, but a semantically charged, critical design component that inflected the stratified spaces of churches in myriad ways. The friezes encapsulated and promoted core aspects of the Christian faith for medieval beholders, evoking the viridity of the paradisiacal garden, Christ as the True Vine, the Eucharistic wine and ritual, and the golden vine of the Temple of Jerusalem, originally built by the wise King Solomon. By situating the proliferation of foliate friezes within the context of the Crusades, moreover, this study provides new insights into the networks of exchange between France, Byzantium, and the Levant, and contributes substantially to the “global turn” in the field of medieval art and architectural history.

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Book chapters on the topic "Lithium amides"

1

Malhotra, Sanjay V. "Asymmetric Catalysis with Chiral Lithium Amides." In ACS Symposium Series, 189–98. Washington, DC: American Chemical Society, 2004. http://dx.doi.org/10.1021/bk-2004-0880.ch013.

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2

Harrison-Marchand, Anne, and Jacques Maddaluno. "Advances in the Chemistry of Chiral Lithium Amides." In Lithium Compounds in Organic Synthesis, 297–328. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2014. http://dx.doi.org/10.1002/9783527667512.ch10.

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3

Leroux, Frédéric R., and Jacques Mortier. "Directed Metalation of Arenes with Organolithiums, Lithium Amides, and Superbases." In Arene Chemistry, 741–76. Hoboken, NJ: John Wiley & Sons, Inc, 2015. http://dx.doi.org/10.1002/9781118754887.ch26.

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4

Hodgson, David M., and Matthew A. H. Stent. "Overview of Organolithium-Ligand Combinations and Lithium Amides for Enantioselective Processes." In Organolithiums in Enantioselective Synthesis, 1–20. Berlin, Heidelberg: Springer Berlin Heidelberg, 2003. http://dx.doi.org/10.1007/3-540-36117-0_1.

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5

Vogt, J. "798 H2LiN Lithium amide." In Asymmetric Top Molecules. Part 3, 399. Berlin, Heidelberg: Springer Berlin Heidelberg, 2011. http://dx.doi.org/10.1007/978-3-642-14145-4_220.

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6

Amonoo-Neizer, E. H., R. A. Shaw, D. O. Skovlin, B. C. Smith, Joel W. Rosenthal, and William L. Jolly. "Lithium Bis(trimethylsilyl)amide and Tris(trimethylsilyl)amine." In Inorganic Syntheses, 19–22. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2007. http://dx.doi.org/10.1002/9780470132395.ch6.

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7

Simpkins, N. S. "Asymmetric deprotonation reactions using enantiopure lithium amide bases." In Advanced Asymmetric Synthesis, 111–25. Dordrecht: Springer Netherlands, 1996. http://dx.doi.org/10.1007/978-94-007-0797-9_6.

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8

Lawson, D. F., D. R. Brumbaugh, M. L. Stayer, J. R. Schreffler, T. A. Antkowiak, D. Saffles, K. Morita, Y. Ozawa, and S. Nakayama. "Anionic Polymerization of Dienes Using Homogeneous Lithium Amide (N-Li) Initiators, and Determination of Polymer-Bound Amines." In ACS Symposium Series, 77–87. Washington, DC: American Chemical Society, 1998. http://dx.doi.org/10.1021/bk-1998-0696.ch006.

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Kalamkar, Rohan, Vivek Yakkundi, and Aneesh Gangal. "Hydrogen Storage Characteristics of Mixture of Lithium Amide and Lithium Hydride Using Severt’s Type Apparatus." In Techno-Societal 2018, 1037–44. Cham: Springer International Publishing, 2019. http://dx.doi.org/10.1007/978-3-030-16848-3_96.

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Harrison-Marchand, Anne, Nicolas Duguet, Gabriella Barozzino-Consiglio, Hassan Oulyadi, and Jacques Maddaluno. "Dynamics of the Lithium Amide/Alkyllithium Interactions: Mixed Dimers and Beyond." In Organo-di-Metallic Compounds (or Reagents), 43–61. Cham: Springer International Publishing, 2014. http://dx.doi.org/10.1007/3418_2014_75.

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Conference papers on the topic "Lithium amides"

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Ji, Lianmin, Lijuan Li, Dong Shi, Jinfeng Li, Defang Xu, Xuexue Song, Zhiqi Liu, Feng Nie, Zhongmin Zeng, and Fugen Song. "Recovery of Lithium Using a novel amide-neutral phosphorus-based extraction system with response surface methodology optimization." In 2016 3rd International Conference on Materials Engineering, Manufacturing Technology and Control. Paris, France: Atlantis Press, 2016. http://dx.doi.org/10.2991/icmemtc-16.2016.17.

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Radivoy, Gabriel, Francisco Alonso, Miguel Yus, Viviana Dorn, Adriana Pierini, Andrés Ciolino, Yanina Moglie, and Fabiana Nador. "Reductive amination of aldehydes using a lithium-arene(cat.) reducing system. A simple one-pot procedure for the synthesis of secondary amines." In The 15th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2011. http://dx.doi.org/10.3390/ecsoc-15-00678.

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3

Jackson, Roderick, Scott Curran, Paul Chambon, Brian Post, Lonnie Love, Robert Wagner, Burak Ozpineci, et al. "Overview of the Oak Ridge National Laboratory Advanced Manufacturing Integrated Energy Demonstration Project: Case Study of Additive Manufacturing as a Tool to Enable Rapid Innovation in Integrated Energy Systems." In ASME 2016 International Mechanical Engineering Congress and Exposition. American Society of Mechanical Engineers, 2016. http://dx.doi.org/10.1115/imece2016-66256.

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Oak Ridge National Laboratory’s Additive Manufacturing Integrated Energy (AMIE) demonstration project leverages rapid innovation through additive manufacturing to connect a natural-gas-powered hybrid electric vehicle to a high-performance building designed to produce, consume, and store renewable energy. The AMIE demonstration project consists of a building and vehicle that were additively manufactured (3D-printed) using the laboratory’s big area additive manufacturing (BAAM) capabilities and an integrated energy system with smart controls that connects the two via wireless power transfer. The printed utility vehicle features a hybrid electric powertrain with onboard power generation from a natural gas fueled auxiliary power unit (APU). The APU extends vehicle range through a series hybrid powertrain configuration that recharges the vehicle’s lithium-ion energy storage system and acts as a mobile power generation system for the printed building. The development of the powertrain used for the printed range-extended electric vehicle was completed using a powertrain-in-the-loop development process and the vehicle prototype implementation was accelerated using BAAM. A flexible 3.2 kW solar photovoltaic system paired with electric vehicle batteries will provide renewable power generation and storage. Energy flows back and forth between the car and house using fast, efficient bidirectional wireless power transfer. The AMIE project marked the first demonstration of bidirectional level 2 charging through wireless power transfer. The accelerated creation and printing of the car and house will further demonstrate the program’s function as an applied science tool to get products to market more quickly than what currently is possible with traditional manufacturing. This paper presents a case study that summarizes the efforts and technical details for using the printed research platforms. This paper explores the focuses on printing of the vehicle, powertrain integration, and possibilities for vehicles providing power to buildings in different scenarios. The ability for BAAM to accelerate the prototype development for the integrated energy system process is explored. Details of how this was successfully accomplished in 9 months with more than 20 industry partners are discussed.

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