53526-74-2Relevant articles and documents
Three-Component Aminoarylation of Electron-Rich Alkenes by Merging Photoredox with Nickel Catalysis
Jiang, Heng,Yu, Xiaoye,Daniliuc, Constantin G.,Studer, Armido
supporting information, p. 14399 - 14404 (2021/05/26)
A three-component 1,2-aminoarylation of vinyl ethers, enamides, ene-carbamates and vinyl thioethers by synergistic photoredox and nickel catalysis is reported. 2,2,2-Trifluoroethoxy carbonyl protected α-amino-oxy acids are used as amidyl radical precursors. anti-Markovnikov addition of the amidyl radical to the alkene and Ni-mediated radical/transition metal cross over lead to the corresponding 1,2-aminoarylation product. The radical cascade, which can be conducted under practical and mild conditions, features high functional group tolerance and broad substrate scope. Stereoselective 1,2-aminoarylation is achieved using a L-(+)-lactic acid derived vinyl ether as the substrate, offering a novel route for the preparation of protected enantiopure α-arylated β-amino alcohols. In addition, 1,2-aminoacylation of vinyl ethers is achieved by using an acyl succinimide as the electrophile for the Ni-mediated radical coupling.
(S)-(-)-N-(Pentafluorobenzylcarbamoyl)prolyl chloride: A chiral derivatisation reagent designed for gas chromatography/negative ion chemical ionisation mass spectrometry of amino compounds
Leis, Hans J.,Windischhofer, Werner
experimental part, p. 592 - 598 (2012/06/29)
RATIONALE The synthesis of a novel chiral derivatisation reagent, (S)-(-)-N-(pentafluorobenzylcarbamoyl)prolyl chloride is described which is preferably useful for negative-ion chemical ionisation mass spectrometry. METHODS Preparation of the reagent followed a general strategy used to prepare enantioselective reagents based on the N-substitution of L-proline. Pentafluorobenzyl chloroformate smoothly reacted with L-proline to give the desired derivatisation reagent after conversion into the acyl chloride. The product was sufficiently pure to be used in the following steps without any additional purification. RESULTS The reagent was tested against selected chiral and non-chiral analytical targets. Chromatographic enantioseparation was at least equal to the commonly used (S)-(-)-N-(heptafluorobutyryl)prolyl derivatives. The derivatives exhibit excellent mass spectral properties under negative ion chemical ionisation, i.e. reduced fragmentation and thus high ion current for the targeted m/z during analysis. With electron ionisation, the fragmentation that occurs is mainly directed by the introduced group. Enantioseparation with gas chromatography/negative-ion chemical ionisation mass spectrometry of the derivatives was demonstrated for the enantiomers of amphetamine, α-aminocaprylic acid methyl ester and threo-methylphenidate. CONCLUSIONS The new derivatisation reagent shows highly improved mass spectral properties for negative-ion chemical ionisation mass spectrometry and is thus suitable for sensitive chiral detection of amino compounds. The reagent extends the applicability of dissociative resonance electron capture using pentafluorobenzyl derivatives to chiral analysis. Copyright
SYNTHESIS OF NITROGEN ANALOGS OF PHENVALERATE
Galin, F. Z.,Ignatyuk, V. K.,Rakhimov, R. G.,Amirkhanov, D. V.,Poskryakov, A. V.,et al.
, p. 1555 - 1557 (2007/10/02)
-