- One-pot biocatalytic amine transaminase/acyl transferase cascade for aqueous formation of amides from aldehydes or ketones
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An efficient one-pot one-step biocatalytic amine transaminase/acyl transferase cascade for the formation of amides from the corresponding aldehydes and ketones in aqueous solution has been developed. N-Benzyl-2-methoxyacetamide has been synthesized utilizing the developed cascade with conversions up to 97%. The cascade was also evaluated for the synthesis of chiral amides.
- Land, Henrik,Hendil-Forssell, Peter,Martinelle, Mats,Berglund, Per
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p. 2897 - 2900
(2016/05/24)
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- Polymer-anchored Ru(II) complex as an efficient catalyst for the synthesis of primary amides from nitriles and of secondary amides from alcohols and amines
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A polymer-anchored ruthenium(II) catalyst was synthesized and characterized. Its catalytic activity was evaluated for the preparation of primary amides from aqueous hydration of nitriles in neutral condition. A range of nitriles were successfully converted to their corresponding amides in good to excellent yields. The catalyst was also effective in the preparation of secondary amides from the coupling of alcohols and amines. The catalyst can be facilely recovered and reused six times without a significant decrease in its activity.
- Islam, Sk Manirul,Ghosh, Kajari,Roy, Anupam Singha,Molla, Rostam Ali
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p. 900 - 907
(2015/02/19)
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- Catalytic acceptorless dehydrogenations: Ru-Macho catalyzed construction of amides and imines
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A commercially available ruthenium(II) PNP type pincer catalyst (Ru-Macho) promotes formation of amides and imines from alcohols and amines via an acceptorless dehydrogenation pathway. The formation of secondary amides, tertiary amides, and secondary ketimines occurs in yields ranging from 35% to 95%.
- Oldenhuis, Nathan J.,Dong, Vy M.,Guan, Zhibin
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supporting information
p. 4213 - 4218
(2014/06/09)
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- Ruthenium-catalysed oxidation of alcohols to amides using a hydrogen acceptor
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A wider investigation into the synthesis of secondary amides from primary alcohols using a hydrogen acceptor using commercially available [Ru(p-cymene)Cl2]2 with bis(diphenylphosphino)butane (dppb) as the catalyst. The report looks at over 50 examples with varying functionality and steric bulk, whilst also covering the first reported results using microwave heating to effect the transformation.
- Watson, Andrew J.A.,Wakeham, Russell J.,Maxwell, Aoife C.,Williams, Jonathan M.J.
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supporting information
p. 3683 - 3690
(2014/05/20)
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- Simple RuCl3-catalyzed amide synthesis from alcohols and amines
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A catalyst for the direct synthesis of amides from amines and alcohols, generated in situ from the economically attractive and readily available RuCl3, an N-heterocyclic carbene (NHC), and pyridine, was developed. Of the screened NHC precursors, a less bulky one gave better yields for modestly sterically hindered substrates. In a search for the true catalytic intermediates, Grubbs catalysts were found to be active for the amidation of alcohols under basic conditions, suggesting that an Ru complex supported by an NHC ligand can catalyze the reaction.
- Ghosh, Subhash Chandra,Hong, Soon Hyeok
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experimental part
p. 4266 - 4270
(2010/09/20)
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- Ruthenium-catalyzed oxidation of alcohols into amides
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The synthesis of secondary amides from primary alcohols and amines has been developed using commercially available [Ru(p-cymene)CI2]2 with bis(diphenylphosphino)butane (dppb) as the catalyst.
- Watson, Andrew J.A.,Maxwell, Aoife C.,Williams, Jonathan M.J.
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supporting information; experimental part
p. 2667 - 2670
(2009/10/02)
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- PROCESS FOR PREPARING AMIDES FROM ALCOHOLS AND AMINES
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The present invention provides a process for preparing amides, by reacting a primary amine and a primary alcohol in the presence of a Ruthenium catalyst, to generate the amide and molecular hydrogen. According to the process of the invention, primary amines are directly acylated by equimolar amounts of alcohols to produce amides and molecular hydrogen (the only byproduct) in high yields and high turnover numbers. This reaction is catalyzed by a Ruthenium complex, which is preferably based on a dearomatized PNN-type ligand of formula A1 or precursors thereof of formulae A2 or A3. Use of diamines in the reaction leads to bis-amides, whereas with a mixed primary/secondary amine substrate, chemoselective acylation of the primary amine group occurs.
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Page/Page column 7-8; 11
(2009/05/28)
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- Synthesis and reactivity of 1-substituted 2-fluoro- and 2,2-difluoroaziridines
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(Chemical Equation Presented) A straightforward synthesis toward 2-fluorinated aziridines was developed via ring closure of β-fluorinated β-chloroamines, which were obtained via reduction of the corresponding α-fluorinated amides by borane. When 1-benzyl-2-fluoroaziridine was treated with methanol, reaction occurred at the 2-position, giving rise to N-benzyl-2,2-dimethoxyethylamine, while in the case of 1-benzyl-2,2- difluoroaziridine the 3-position was attacked, giving rise to N-benzyl-2-methoxyacetamide. These reactions point to the divergent reactive behavior of monofluoro- and difluoroaziridines.
- Verniest, Guido,Colpaert, Filip,Van Hende, Eva,De Kimpe, Norbert
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p. 8569 - 8572
(2008/02/13)
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- Synthesis of enantiopure imidazolines through a Ritter reaction of 2-(1-aminoalkyl)aziridines with nitriles
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(Chemical equation presented) The Ritter reaction of enantiopure 2-(1-aminoalkyl)aziridines 1 with different nitriles afford enantiopure tetrasubstituted imidazolines 2. The opening of the aziridine ring takes place with total regio- and stereoselectivity. A mechanism to explain the described addition reaction is proposed.
- Concellon, Jose M.,Riego, Estela,Suarez, Jose Ramon,Garcia-Granda, Santiago,Diaz, M. Rosario
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p. 4499 - 4501
(2007/10/03)
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- Glycono-1,3-lactams, Xylo Series: Stereoselective Access by Cycloaddition, Exploratory Transformations, and Discovery of a New, Highly Selective Inhibitor of Glucoamylases
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Cycloaddition of chiral imines 4-7, derived from 2-O-benzylglyceraldehyde, with α-alkoxy ketenes 1-3 furnished 3-amino-3-deoxy-glycono-1,3-lactams 8-15 (50-78 percent) with 2,3-cis configuration in diastereomeric ratios of 87 : 13 to > 95 : 5.From these O,N-deprotected β-lactams 16-18 were prepared.Reduction of the xylono-1,3-lactam 18 using monochloroalane (ClAlH2) produced the corresponding azetidine 19, while reduction of 14 with LiAlH4 gave the aminotetrol derivative 20.Treatment of the β-lactam triol 21 with NaIO4 led to the 3,4-dihydro-2H-1,4-oxazine-3-one 22, via cleavage of the C2-C3 bond and recyclization.The 1,3-imino-xylitol 19 exhibited highly selective inhibition of the two gluco-amylases tested (IC50 values of 31 and 4 (M)).
- Kraemer, Bernd,Franz, Thomas,Picasso, Sylviane,Pruschek, Petra,Jaeger, Volker
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p. 295 - 297
(2007/10/03)
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