- Continuous Flow Chiral Amine Racemization Applied to Continuously Recirculating Dynamic Diastereomeric Crystallizations
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A new, dynamic diastereomeric crystallization method has been developed, in which the mother liquors are continuously separated, racemized over a fixed-bed catalyst, and recirculated to the crystallizer in a resolution-racemization-recycle (R3) process. S
- Kwan, Maria H. T.,Breen, Jessica,Bowden, Martin,Conway, Louis,Crossley, Ben,Jones, Martin F.,Munday, Rachel,Pokar, Nisha P. B.,Screen, Thomas,Blacker, A. John
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p. 2458 - 2473
(2021/02/06)
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- Deactivation mechanisms of iodo-iridium catalysts in chiral amine racemization
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The homogenous, [IrCp?I2]2, SCRAM catalyst (1) is active in the racemization of chiral amines. NMR, kinetic and structural mechanistic studies have determined the cause of catalyst deactivation to occur when ammonia or methylamine are liberated by hydrolysis or aminolysis of the intermediate imine, which tightly coordinate to the iridium centre to block turnover. Control of moisture and substrate concentration can suppress deactivation, whilst partial reactivation of spent catalyst was identified using hydroiodic acid.
- Kwan, Maria H.T.,Pokar, Nisha P.B.,Good, Catherine,Jones, Martin F.,Munday, Rachel,Screen, Thomas,Blacker, A. John
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- Imine reduction with me2s-bh3
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Although there exists a variety of different catalysts for hydroboration of organic substrates such as aldehydes, ketones, imines, nitriles etc., recent evidence suggests that tetra-coordinate borohydride species, formed by activation, redistribution, or decomposition of boron reagents, are the true hydride donors. We then proposed that Me2S-BH3 could also act as a hydride donor for the reduction of various imines, as similar compounds have been observed to reduce carbonyl substrates. This boron reagent was shown to be an effective and chemoselective hydroboration reagent for a wide variety of imines.
- Kamal, Mohammad M.,Liu, Zhizhou,Vidovi?, Dragoslav,Zhai, Siyuan
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- Enantioselective reduction of: N -alkyl ketimines with frustrated Lewis pair catalysis using chiral borenium ions
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Enantioselective reduction of ketimines was demonstrated using chiral N-heterocyclic carbene (NHC)-stabilised borenium ions in frustrated Lewis pair catalysis. High levels of enantioselectivity were achieved for substrates featuring secondary N-alkyl substituents. Comparative reactivity and mechanistic studies identify key determinants required to achieve useful enantioselectivity and represent a step forward in the further development of enantioselective FLP methodologies.
- Mercea, Dan M.,Howlett, Michael G.,Piascik, Adam D.,Scott, Daniel J.,Steven, Alan,Ashley, Andrew E.,Fuchter, Matthew J.
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supporting information
p. 7077 - 7080
(2019/06/20)
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- Transformation of N,N-diisopropylarylmethylamines into N-isopropylarylmethylamines with molecular iodine
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N,N-Diisopropylarylmethylamines were smoothly converted into the corresponding N-isopropylarylmethylamines by the reaction with molecular iodine in the presence of Na2CO3 in chloroform at 60 °C. Other related tertiary amines were also transformed into the corresponding secondary amines by the reaction with molecular iodine under the same reaction conditions.
- Ezawa, Masatoshi,Moriyama, Katsuhiko,Togo, Hideo
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p. 6689 - 6692
(2016/02/03)
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- Synthesis and structure-activity relationship of disubstituted benzamides as a novel class of antimalarial agents
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Malaria is a devastating world health problem. Using a compound library screening approach, we identified a novel series of disubstituted benzamide compounds with significant activity against malaria strains 3D7 and K1. These compounds represent a new antimalarial molecular scaffold exemplified by compound 1, which demonstrated EC50 values of 60 and 430 nM against strains 3D7 and K1, respectively. Herein we report our findings on the efficient synthesis, structure-activity relationships, and biological activity of this new class of antimalarial agents.
- Mitachi, Katsuhiko,Salinas, Yandira G.,Connelly, Michele,Jensen, Nicholas,Ling, Taotao,Rivas, Fatima
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p. 4536 - 4539
(2012/08/07)
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- Iridium-catalysed amine alkylation with alcohols in water
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Amines have been directly alkylated with alcohols using 1 mol% [Cp*IrI2]2 catalyst in water in the absence of base or other additives. The Royal Society of Chemistry 2010.
- Saidi, Ourida,Blacker, A. John,Farah, Mohamed M.,Marsden, Stephen P.,Williams, Jonathan M. J.
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supporting information; experimental part
p. 1541 - 1543
(2010/06/12)
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- Monoalkylation of primary amines and N-sulfinylamides
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An efficient monoalkylation of primary amines with primary or secondary alcohols catalyzed by Ra-Ni under mild conditions is described. The Royal Society of Chemistry.
- García Ruano, José Luis,Parra, Alejandro,Alemán, José,Yuste, Francisco,Mastranzo, Virginia M.
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supporting information; experimental part
p. 404 - 406
(2009/05/06)
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- ASYMMETRIC IMINE HYDROGENATION PROCESSES
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A process for the catalytic hydrogenation or asymmetric hydrogenation of imines of Formula (I) to the corresponding amines of Formula (II) is provided in which R1 is aryl ; R2 is aryl, cyclic, alkyl, alkenyl or alkynyl; and R3 is alky l. The catalytic system includes a ruthenium complex containing (1) a diamine and (2) a diphosphine or two monodentate phosphines ligands. Such process also relates to the asymmetric hydrogenation of prochiral imines to the chiral amines using chiral ruthenium complexes bearing chiral diphosphines or chiral monodentate phosphines and chiral diamines.
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Page/Page column 29
(2008/06/13)
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- Hydroamination of carbonyl compounds with oximes
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N-alkyl(cycloalkyl)benzylamines, p-fluorobenzylamines, (1-phenylethyl) amines, [1-(p-fluorophenyl)ethyl]amines were synthesized by hydroamination of aldehydes and ketones with oximes.
- Tarasevich,Kozlov
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p. 379 - 383
(2007/10/03)
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- Synthesis of [11C]/(13C)amines via carbonylation followed by reductive animation
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Twelve 11C-labelled amines were prepared via 11C-carbonylation followed by reductive amination. The 11C-carbonylation was performed in the presence of tetrakis(triphenylphosphine)palladium using aryl iodides or aryl trifla
- Rahman, Obaidur,Kihlberg, Tor,Langstroem, Bengt
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p. 1612 - 1616
(2007/10/03)
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- Synthesis of 2,2-Dichloro-1,3-diarylaziridines by Reduction of Trichloroacetophenone Imines
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2,2-Dichloro-1,3-diarylaziridines, usually obtained by addition of dichlorocarbene to benzylideneanilines, were synthesized by reaction of N-aryl-α,α,α-trichloroacetophenone imines with lithium aluminium hydride in ether.
- Kimpe, Norbert De,Verhe, Roland,Buyck, Laurent De,Schamp, Niceas
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p. 2079 - 2081
(2007/10/02)
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- Novel Synthetic Reactions Using Bis(2,2,2-trifluoroethoxy)triphenylphosphorane
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Alkoxy-or (acyloxy)(2,2,2-trifluoroethoxy)triphenylphosphoranes which were prepared in situ by the ligand exchange of bis(2,2,2-trifluoroethoxy)triphenylphosphorane with alcohols or carboxylic acids were found to behave as potential alkylating or acylating reagents for the preparation of a variety of esters, amides, sulfides, and ketones.
- Kubota, Toshio,Miyashita, Satoshi,Kitazume, Tomoya,Ishikawa, Nobuo
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p. 5052 - 5057
(2007/10/02)
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