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Journal articles on the topic 'Lithium amides'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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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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2

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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5

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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11

Fressigné, Catherine, Jacques Maddaluno, Claude Giessner-Prettre, and Bernard Silvi. "Why Are Monomeric Lithium Amides Planar?" Journal of Organic Chemistry 66, no. 19 (September 2001): 6476–79. http://dx.doi.org/10.1021/jo010451h.

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12

Ang, KH, RH Prager, and CM Williams. "The Chemistry of 5-Oxodihydroisoxazoles. XII. Trapping of Derived Ketenimines With Lithium Amides and Alkyllithiums." Australian Journal of Chemistry 48, no. 1 (1995): 55. http://dx.doi.org/10.1071/ch9950055.

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Isoxazolones unsubstituted at C3 react with lithium amides or alkyllithiums to give ketenimines . The presence of an ethoxycarbonyl group at C4 allows capture of this species by addition of a second equivalent of the lithiated species to give enolates which can be alkylated in situ. The presence of a phenyl group at C4 gives a ketenimine which reacts intramolecularly in the presence of lithium amides, whereas alkyllithiums undergo addition in synthetically useful processes.

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13

Majewski, Marek, D. Mark Gleave, and Pawel Nowak. "1,3-Dioxan-5-ones: synthesis, deprotonation, and reactions of their lithium enolates." Canadian Journal of Chemistry 73, no. 10 (October 1, 1995): 1616–26. http://dx.doi.org/10.1139/v95-201.

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A general synthetic route to 2-alkyl- and 2,2-dialkyl-1,3-dioxan-5-ones, using tris(hydroxymethyl)-nitromethane as the starting material, is described. Deprotonation of these compounds was studied. It was established that these dioxanones could be deprotonated with LDA; however, the reduction of the carbonyl group via a hydride transfer from LDA, giving the corresponding dioxanols, often competed with deprotonation. The reduction could be minimized by using Corey's internal quench procedure to form silyl enol ethers and was less pronounced in 2,2-dialkyldioxanones (ketals) than in 2-alkyldioxanones (acetals). Self-aldol products were observed when dioxanone lithium enolates were quenched with H2O. Addition reactions of lithium enolates of dioxanones to aldehydes were threo-selective as predicted by the Zimmerman–Traxler model. Dioxanones having two different alkyl groups at the 2-position were deprotonated enantioselectively by chiral lithium amide bases with enantiomeric excess (ee) of up to 70%. Keywords: 1,3-dioxan-5-ones, enantioselective deprotonation, chiral lithium amides.

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14

Bennett, Ryan M., Wei Sun, Dharyl C. Wilson, Mark E. Light, and David C. Harrowven. "A new mode of cyclobutenedione ring opening for the synthesis of 2-oxobut-3-enamides and tetrasubstituted furans." Chemical Communications 57, no. 46 (2021): 5694–97. http://dx.doi.org/10.1039/d1cc02097h.

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The addition of lithium amides to cyclobutenediones provides access to 2-oxo-but-3-enamides and tetrasubstituted furans via a new mode of ring opening involving enone cleavage via O- to C-lithium transfer.

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15

Chen, Ye Chuan, Guang Yang, Rui Zhao, and Wei Dong Xue. "Improved Low Temperature Solution Synthesis of Silicon Nanoparticles for Lithium-Ion Batteries." Materials Science Forum 809-810 (December 2014): 180–86. http://dx.doi.org/10.4028/www.scientific.net/msf.809-810.180.

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Silicon nanoparticles have extraordinary electrochemical performance for lithium-ion batteries. This paper gives an improved low temperature solution synthesis route of Si NPs. Reduced by magnesium and then passivated by four kinds of amines/amides respectively, stable yellow Si NPs ranging from 5-50 nm were prepared. When passivated by N-methyl-2-pyrrolidone, grape-like aggregation of 5-20 nm particles were generated. FTIR, XRD, SEM and Electrochemical Characterization were performed to confirm the product. The Si NPs passivated by NMP achieve good electrochemical performance with a first discharge capacity of 1154 mAhg-1at a current density of 200 mAg-1and good capacity retention of 95.3% after 5 cycles.

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16

Hedidi, Madani, Gandrath Dayaker, Yu Kitazawa, Tatsuya Yoshii, Mutsumi Kimura, William Erb, Ghenia Bentabed-Ababsa, et al. "Enantioselective deprotometalation of N,N-dialkyl ferrocenecarboxamides using metal amides." New Journal of Chemistry 43, no. 37 (2019): 14898–907. http://dx.doi.org/10.1039/c9nj03780b.

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17

Barry, Conor S., and Nigel S. Simpkins. "Hydroamination of cinnamyl alcohol using lithium amides." Tetrahedron Letters 48, no. 46 (November 2007): 8192–95. http://dx.doi.org/10.1016/j.tetlet.2007.09.086.

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18

Maddaluno, J., K. Tomioka, N. Duguet, and A. Harrison-Marchand. "Conjugate Addition Catalyzed by Chiral Lithium Amides." Synfacts 2007, no. 3 (March 2007): 0280. http://dx.doi.org/10.1055/s-2007-968240.

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19

Kaizer, E. B., N. G. Kravchenko, and A. S. Poplavnoi. "Elastic Properties of Lithium and Sodium Amides." Russian Physics Journal 61, no. 9 (December 26, 2018): 1695–701. http://dx.doi.org/10.1007/s11182-018-1589-x.

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20

Green, James R., Marek Majewski, and Victor Snieckus. "Deprotonation of β,β-disubstituted α,β-unsaturated amides - Mechanism and stereochemical consequences." Canadian Journal of Chemistry 84, no. 10 (October 1, 2006): 1397–410. http://dx.doi.org/10.1139/v06-112.

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A detailed study of the lithium dialkylamide induced deprotonation of β,β-disubstituted α,β-unsaturated amides is presented. The preferential γ-Z-deprotonation and stereochemical outcome of substituents on the γ-Z carbon atom are rationalized in terms of a cyclic eight-membered transition state, which is supported by DFT calculations. Analogous deprotonations on cyclohexylidenecarboxamides reveal a delicate balance of the preference for the eight-membered cyclic transition state with the effects of existing substituents on the ring and the intervention of a twist-boat transition state.Key words: dienolate, amide, deprotonation mechanism, transition state, enolization, regioselectivity, stereoselectivity.

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21

Sott, Richard, Johan Granander, Peter Dinér, and Göran Hilmersson. "Solution structures of chiral lithium amides with internal sulfide coordination: sulfide versus ether coordination in chiral lithium amides." Tetrahedron: Asymmetry 15, no. 2 (January 2004): 267–74. http://dx.doi.org/10.1016/j.tetasy.2003.11.009.

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22

Martínez-Martínez, Antonio J., Alan R. Kennedy, Valerie Paprocki, Felipe Fantuzzi, Rian D. Dewhurst, Charles T. O’Hara, Holger Braunschweig, and Robert E. Mulvey. "Selective mono- and dimetallation of a group 3 sandwich complex." Chemical Communications 55, no. 65 (2019): 9677–80. http://dx.doi.org/10.1039/c9cc03825f.

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While lithium alkyls and lithium amides do not metallate the scandium compound [(η⁵-C₅H₅)Sc(η⁸-C₈H₈)], a synergistic lithium–aluminium base-trap partnership cannot resist taking a bite with one C–H bond selectively cleaved from both Cp and COT rings.

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23

Zhao, Ru, Bing-Lin Zeng, Wen-Qiang Jia, Hong-Yi Zhao, Long-Ying Shen, Xiao-Jian Wang, and Xian-Dao Pan. "LiCl-promoted amination of β-methoxy amides (γ-lactones)." RSC Advances 10, no. 57 (2020): 34938–42. http://dx.doi.org/10.1039/d0ra07170f.

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24

Vejdělek, Zdeněk, Jiří Němec, and Miroslav Protiva. "Synthesis of N-(1-phenyl-2-propyl)-2,5-diphenylpentylamine and some related compounds as potential neurotropic and cardiovascular drugs." Collection of Czechoslovak Chemical Communications 51, no. 7 (1986): 1487–93. http://dx.doi.org/10.1135/cccc19861487.

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Heating of 2,5-diphenylvaleric acid with 2-phenylethylamine, 1-phenyl-2-propylamine, 1-phenyl-2-butylamine (IX), 1-(4-methoxyphenyl)-2-propylamine, 1-(4-methoxyphenyl)-2-butylamine (X) and 1-(4-dimethylaminophenyl)-2-propylamine to 200-210 °C resulted in the amides IIb-VIIb which were reduced with lithium aluminium hydride in boiling dibutyl ether to give the amines IIa, IIIa, and Va - VIIa. A similar two-step sequence starting from 4-phenyl-4-(phenylthio)-butyric acid and the amine IX gave compound VIIIa. The salts of the title amines revealed some central stimulating, antireserpine, thiopental potentiating, anticonvulsant, and antiarrhythmic effects. 1-(4-Dimethylaminophenyl)-2-butylamine (XI), prepared in this connection, proved anoretic activity.

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25

Miller, Shelli A., and Nicholas E. Leadbeater. "Direct, rapid, solvent-free conversion of unactivated esters to amides using lithium hydroxide as a catalyst." RSC Advances 5, no. 113 (2015): 93248–51. http://dx.doi.org/10.1039/c5ra21394k.

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26

Zechovský, Jan, Ondřej Mrózek, Maksim Samsonov, Roman Jambor, Aleš Růžička, and Libor Dostál. "Coordination capabilities of bis-(2-pyridyl)amides in the field of divalent germanium, tin and lead compounds." Dalton Transactions 50, no. 18 (2021): 6321–32. http://dx.doi.org/10.1039/d1dt00717c.

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27

Asami, Masatoshi, and Atsushi Seki. "An Intriguing Effect of Polymer-Bound Lithium Amides in Catalytic Enantioselective Rearrangement ofmeso-Epoxides Mediated by Chiral Lithium Amides." Chemistry Letters 31, no. 2 (February 2002): 160–61. http://dx.doi.org/10.1246/cl.2002.160.

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28

van Vliet, Gerbert L. J., Henri Luitjes, Marius Schakel, and Gerhard W. Klumpp. "Lithium Amides: Intra-Aggregate Complexation of Lithium and Entropy Control of Basicity." Angewandte Chemie International Edition 39, no. 9 (May 2, 2000): 1643–45. http://dx.doi.org/10.1002/(sici)1521-3773(20000502)39:9<1643::aid-anie1643>3.0.co;2-9.

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29

Tomioka, K., T. Sakai, and Y. Kawamoto. "Ligand-Controlled Asymmetric Conjugate Addition of Lithium Amides." Synfacts 2006, no. 9 (September 2006): 0942. http://dx.doi.org/10.1055/s-2006-949216.

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30

Hodgson, David M., Christopher D. Bray, and Nicholas D. Kindon. "Enamines from Terminal Epoxides and Hindered Lithium Amides." Journal of the American Chemical Society 126, no. 22 (June 2004): 6870–71. http://dx.doi.org/10.1021/ja031770o.

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31

Rutherford, Drew, and David A. Atwood. "Unusual Alkylaluminum Amides, Adducts, and Aluminates Containing Lithium." Journal of the American Chemical Society 118, no. 46 (January 1996): 11535–40. http://dx.doi.org/10.1021/ja961244f.

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32

Scott, Natalie M., Thomas Schareina, Oleg Tok, and Rhett Kempe. "Lithium and Potassium Amides of Sterically Demanding Aminopyridines." European Journal of Inorganic Chemistry 2004, no. 16 (August 2004): 3297–304. http://dx.doi.org/10.1002/ejic.200400228.

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33

KOGA, K. "ChemInform Abstract: Enantioselective Reactions Using Chiral Lithium Amides." ChemInform 28, no. 4 (August 4, 2010): no. http://dx.doi.org/10.1002/chin.199704309.

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34

Seki, Atsushi, Youichi Takizawa, Fusae Ishiwata, and Masatoshi Asami. "Crossed Aldol Reaction Using Polymer-bound Lithium Amides." Chemistry Letters 32, no. 4 (April 2003): 342–43. http://dx.doi.org/10.1246/cl.2003.342.

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35

Williard, P., and L. Ma. "Asymmetric Deprotonation Using Polymer-Supported Chiral Lithium Amides." Synfacts 2007, no. 3 (March 2007): 0331. http://dx.doi.org/10.1055/s-2007-968226.

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36

Fairley, Michael, Leonie J. Bole, Florian F. Mulks, Laura Main, Alan R. Kennedy, Charles T. O'Hara, Joaquín García-Alvarez, and Eva Hevia. "Ultrafast amidation of esters using lithium amides under aerobic ambient temperature conditions in sustainable solvents." Chemical Science 11, no. 25 (2020): 6500–6509. http://dx.doi.org/10.1039/d0sc01349h.

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Using 2-methyl THF as solvent enables efficient and ultrafast amidation of esters by lithium amides at room temperature in air, edging closer towards reaching air- and moisture-compatible polar organometallic chemistry.

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37

Itsenko, Oleksiy, Elisabeth Blom, Bengt Långström, and Tor Kihlberg. "The Use of Lithium Amides in the Palladium-Mediated Synthesis of [Carbonyl-11C]Amides." European Journal of Organic Chemistry 2007, no. 26 (September 2007): 4337–42. http://dx.doi.org/10.1002/ejoc.200700255.

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38

Tomioka, Kiyoshi, Takeo Sakai, Tokutaro Ogata, and Yasutomo Yamamoto. "Aminolithiation of carbon-carbon double bonds as a powerful tool in organic synthesis." Pure and Applied Chemistry 81, no. 2 (January 1, 2009): 247–53. http://dx.doi.org/10.1351/pac-con-08-08-02.

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A conjugate amination of α,β-unsaturated carbonyl compounds with lithium amides has become a powerful method of N-C bond-forming reactions. Chiral ligand-controlled asymmetric version of the conjugate amination of enoates was developed for practical bench chemistry, giving the enantioenriched amination product with over 99 % ee. In situ diastereoselective alkylation of resulting lithium enolates allowed us to form vicinal N-C and C-C bonds in a one-pot operation. This protocol enabled us to realize a short-step asymmetric synthesis of otamixaban key intermediate. Treatment of product 3-benzylamino- and 3-allylaminoesters with tert-butyllithium gave five- or seven-membered lactams through [1,2]- or [2,3]-rearrangement of intermediate β-lactams. Isolated C-C double bonds were also found to accept intramolecular aminolithiation affording the corresponding hydroamination products. Chiral lithiophilic ligand-catalyzed reaction gave enantioenriched hydroamination products with high ee. Stereoselective intramolecular aminolithiation of allylaminoalkenes was coupled with subsequent carbolithiation to give doubly cyclized product amines.

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39

Arvidsson, Per I., Göran Hilmersson, and Öjvind Davidsson. "Rational Design of Chiral Lithium Amides for Asymmetric Alkylation Reactions-NMR Spectroscopic Studies of Mixed Lithium Amide/Alkyllithium Complexes." Chemistry - A European Journal 5, no. 8 (July 22, 1999): 2348–55. http://dx.doi.org/10.1002/(sici)1521-3765(19990802)5:8<2348::aid-chem2348>3.0.co;2-a.

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40

Arvidsson, Per I., Göran Hilmersson, and Per Ahlberg. "Stereoselective Diamine Chelates of a Chiral Lithium Amide Dimer: New Insights into the Coordination Chemistry of Chiral Lithium Amides." Journal of the American Chemical Society 121, no. 9 (March 1999): 1883–87. http://dx.doi.org/10.1021/ja9827550.

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41

Duguet, Nicolas, Anne Harrison-Marchand, Jacques Maddaluno, and Kiyoshi Tomioka. "Enantioselective Conjugate Addition of a Lithium Ester Enolate Catalyzed by Chiral Lithium Amides." Organic Letters 8, no. 25 (December 2006): 5745–48. http://dx.doi.org/10.1021/ol062270d.

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42

Kazmia, Syed Najam-ul-Hussain, Zaheer Ahmed, Abdul Malik, Nighat Afza, and Wolfgang Voelterc. "A Regioselective One Pot Synthesis and Synthetic Applications of Cyanodeoxy Sugars by Cyanotrimethylsilane." Zeitschrift für Naturforschung B 50, no. 2 (February 1, 1995): 294–302. http://dx.doi.org/10.1515/znb-1995-0225.

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Abstract:

The regioselective epoxide opening of different 2,3-anhydropyranoses by cyanotrimethylsilane is investigated. The isolated cyanodeoxy pyranoses allow easy access to the corresponding branched-chains aminomethyl sugars by lithium aluminium hydride reduction or sugar amides by controlled acid hydrolysis.

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43

ASAMI, Masatoshi. "Asymmetric Transformation of meso-Epoxides by Chiral Lithium Amides." Journal of Synthetic Organic Chemistry, Japan 54, no. 3 (1996): 188–99. http://dx.doi.org/10.5059/yukigoseikyokaishi.54.188.

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44

Fryzuk, Michael D., Garth R. Giesbrecht, Samuel A. Johnson, James E. Kickham, and Jason B. Love. "Chelating amides of lithium. Synthesis, structure and coordination chemistry." Polyhedron 17, no. 5-6 (March 1998): 947–52. http://dx.doi.org/10.1016/s0277-5387(97)00242-8.

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45

REED, F. "ChemInform Abstract: Chiral Lithium Amides Provide Novel Synthetic Routes." ChemInform 22, no. 45 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199145334.

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46

Bertilsson, Sophie K., and Pher G. Andersson. "Asymmetric base-promoted epoxide rearrangement: achiral lithium amides revisited." Tetrahedron 58, no. 23 (June 2002): 4665–68. http://dx.doi.org/10.1016/s0040-4020(02)00372-1.

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47

Pasumansky, Lubov, Armando R. Hernández, Soya Gamsey, Christian T. Goralski, and Bakthan Singaram. "Synthesis of aminopyridines from 2-fluoropyridine and lithium amides." Tetrahedron Letters 45, no. 34 (August 2004): 6417–20. http://dx.doi.org/10.1016/j.tetlet.2004.06.132.

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48

Feit, Ben-Ami, Shulamit Dickerman, Djamal Masrawe, and Ariela Fishman. "Stereoselective addition of lithium amides to activated triple bonds." Journal of the Chemical Society, Perkin Transactions 1, no. 4 (1988): 927. http://dx.doi.org/10.1039/p19880000927.

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49

Withnall, Robert, Ian R. Dunkin, and Ronald Snaith. "Thermal decomposition of lithium amides: a matrix isolation investigation." Journal of the Chemical Society, Perkin Transactions 2, no. 9 (1994): 1973. http://dx.doi.org/10.1039/p29940001973.

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50

Herbst-Irmer, Regine, Uwe Klingebiel, and Mathias Noltemeyer. "2.4.6-Tri-tert-butylphenylaminofluorsilane und Lithium-bis(2,4,6-tri tert- butylphenyldifluorsilyl)amid - im Kristall ein Polymer / 2.4.6-Tri-tert-butylphenylaminofluorosilanes and Lithium-bis(2,4,6-tri-tert-butylphenyldifluorosilyl) amide - in the Crystal a Polymer." Zeitschrift für Naturforschung B 54, no. 3 (March 1, 1999): 314–20. http://dx.doi.org/10.1515/znb-1999-0304.

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Abstract:

2,4,6-Tri-tert-butylphenyltrifluorosilane (1) reacts with lithium amides to give the aminofluorosilanes (2 - 7); RSiF2NHR′ (R = 2,4,6-Me3CC6H2; R′ = H (2), CMe3 (3), SiMe2CMe3 (4)), (R-SiF2)2NH (5), RSiF(NHR′)2. R′ = CMe3 (6), C6H5 (7). The reaction of 5 with BuLi in THF leads to the formation of the monomeric lithium derivative 8, R-SiF2Li⊕(THF)3-N⊖ -SiF2R. The polymeric lithium derivative 9 [R-SiF2-N⊖-SiRF2Li⊕(THF)2]n is obtained by recrystallisation of 8 in THF. In 8 and 9 lithium is only coordinated to fluorine and THF. Hydrolysis of 8 or 9 lead to the 1,3-disiloxane 10, (RSiF2)2O . 10 shows linearity at the oxygen and short Si-O bond lengths.

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