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Organocatalytic enantioselective Pictet-Spengler approach to biologically relevant 1-benzyl-1,2,3,4-tetrahydroisoquinoline alkaloids.
A general procedure for the synthesis of 1-benzyl-1,2,3,4-tetrahydroisoquinolines was developed, based on organocatalytic, regio- and enantioselective Pictet-Spengler reactions (86-92% ee) ofExpand
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The proton affinities of saturated and unsaturated heterocyclic molecules
Abstract The proton affinities derived from G3-calculations of 23 five-membered ring heteroaromatic molecules agree well with the experimentally determined values available in the literature. TheExpand
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Total syntheses of mitragynine, paynantheine and speciogynine via an enantioselective thiourea-catalysed Pictet-Spengler reaction.
The pharmacologically interesting indole alkaloids (-)-mitragynine, (+)-paynantheine and (+)-speciogynine were synthesised in nine steps from 4-methoxytryptamine by a route featuring (i) anExpand
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Proton affinities and heats of formation of the imines CH2NH, CH2NMe and PhCHNH
The proton affinities of the imines CH2NH, CH2NMe and PhCHNH have been determined by Fourier transform ion cyclotron resonance (FT-ICR) mass Spectrometry to be 854 ± 8 kJ mol–1, 880 ± 8 kJ mol–1 andExpand
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The gas-phase acidity of the phenyl radical and some C6H4X·(X = F, Cl, CN) radicals
Fourier transform ion cyclotron resonance (FT–ICR) mass spectrometry has been used to determine the gas-phase acidities (values in parentheses) of the radicals C6H5·(1592 kJ mol–1), C6H4F·(1565 kJExpand
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Enantioselective BINOL-phosphoric acid catalyzed Pictet-Spengler reactions of N-benzyltryptamine.
Optically active tetrahydro-beta-carbolines were synthesized via an ( R)-BINOL-phosphoric acid-catalyzed asymmetric Pictet-Spengler reaction of N-benzyltryptamine with a series of aromatic andExpand
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Non-Equilibrium Isomer Distribution of the Gas-Phase Photoactive Yellow Protein Chromophore.
The conjugate base of para-coumaric acid, which can be conveniently generated in the gas phase by electrospray ionization (ESI), is a commonly used model system for the chromophore of the photoactiveExpand
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Organocatalytic enantioselective Pictet-Spengler reactions for the syntheses of 1-substituted 1,2,3,4-tetrahydroisoquinolines.
A series of 1-substituted 1,2,3,4-tetrahydroisoquinolines was prepared from N-(o-nitrophenylsulfenyl)phenylethylamines through BINOL-phosphoric acid [(R)-TRIP]-catalyzed asymmetric Pictet-SpenglerExpand
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Formation and chemistry of radical anions in the gas phase
The research concerned with the ion/molecule chemistry of radical anions is reviewed together with the thermochemical properties of these ions and the related neutral species. Attention has beenExpand
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