The Preparation of Amines by Reductive Alkylation

Emerson, William S.

doi:10.1002/0471264180.or004.03

Cited by 18 publications

(27 citation statements)

References 87 publications

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“…As a result, the development of synthetic methodologies for the chemo-, regio-, and stereoselective introduction of C–N bonds has been vigorously pursued. 1a–e One attractive approach is the direct insertion of a nitrene or nitrenoid species into a C–H or C=C bond of an unsaturated substrate, and many catalysts based on Rh, Ru, Fe, Co, Cu, Mn, Au, and Ag have been exploited in this context. 2a–m However, chemoselective C–N bond formation in substrates bearing both reactive C–H and C=C bonds is a particularly challenging task, as these compounds (Figure 1) often give rise to multiple products or exhibit substratecontrolled selectivity.…”

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confidence: 99%

Tunable, Chemoselective Amination via Silver Catalysis

et al. 2013

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Organic N-containing compounds, including amines, are essential components of many biologically and pharmaceutically important molecules. One strategy for introducing nitrogen into substrates with multiple reactive bonds is to insert a monovalent N fragment (nitrene or nitrenoid) into a C–H bond or add it directly to a C=C bond. However, it has been challenging to develop well-defined catalysts capable of promoting predictable and chemoselective aminations solely through reagent control. Herein, we report remarkable chemoselective aminations that employ a single metal (Ag) and a single ligand (phenanthroline) to promote either aziridination or C–H insertion by manipulating the coordination geometry of the active catalysts.

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confidence: 99%

Tunable, Chemoselective Amination via Silver Catalysis

et al. 2013

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“…Treatment with 6-oxo-nheptanoic acid 13 and dicyclohexylcarbodiimide (12) gave the ketoamides 14 and 15 which were transformed to the conjugates 16 and 17 by reductive amination with norepinephrine over Adam's catalyst (platinum dioxide) (13) in acetic acid. N-Acetyl-p-aminophenylalanine hydroxypropylamide 11 was prepared by treating the methyl ester of N-acetyl-L-pnitrophenylalanine 7 with an excess of 3-amino-1-propanol at room temperature, followed by reduction (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

Conjugates of catecholamines. III. Synthesis and characterization of monodisperse oligopeptides conjugates related to isoproterenol

Jacobson

Verlander

Rosenkranz

et al. 1983

International Journal of Peptide and Protein Research

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A series of monodisperse oligopeptide conjugates related to the catecholamine, isoproterenol, has been synthesized. The peptide carrier molecules used were synthesized by stepwise and fragment condensation techniques and ranged in size from a single, blocked amino acid derivative to isomeric pentapeptides. The amino acid compositions and sequences of the carriers were chosen so as to provide specific information concerning the effects of molecular weight, hydrophilic/hydrophobic balance, charge, etc., on the biological activity of the final conjugates. The common point of attachment for the drug in all carriers was a p-aminophenylalanine residue. The peptide-catecholamine conjugates were prepared via the attachment of carboxyl-containing catecholamine congeners, to the peptide carriers by techniques described previously. The conjugates were purified rigorously by chromatographic techniques and characterized by high-field n.m.r. spectroscopy.

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“…Besides the classical Leuckart-Wallach or Eschweiler-Clarke procedures, 1 this reaction is normally performed in organic solvents using several borohydride reagents 2 or catalytic hydrogenation. 3 We decided to study the electrorreductive methylation reaction, by means of aqueous formaldehyde motivated by the good results of our reaction promoted by zinc 4 and due to the scarce reports on the electrochemical strategy in the literature. …”

Section: Introductionmentioning

confidence: 99%