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3-Chloroperbenzoic Acid

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Kilian Muñiz – One of the best experts on this subject based on the ideXlab platform.

  • A Practical Aryliodine(I/III) Catalysis for the Vicinal Diamination of Styrenes.
    ChemSusChem, 2019
    Co-Authors: Eric Cots, Andrea Flores, R. Martín Romero, Kilian Muñiz
    Abstract:

    2,6-Disubstituted iodoarenes bearing amide-functionalized side arms are reported as new structures in redox-active iodine(I/III) catalysis. In combination with bis-sulfonimides as nitrogen sources and 3-Chloroperbenzoic Acid (mCPBA) as benign terminal oxidant they catalyze the vicinal diamination of styrenes. The obtained reactivity and selectivity outperform other iodoarene catalyst candidates. This protocol provides a sustainable alternative to previous related protocols for diamination that are based on stoichiometric iodine(III) reagents.

  • Catalytic Asymmetric Diamination of Styrenes
    Journal of the American Chemical Society, 2017
    Co-Authors: Kilian Muñiz, R. Martín Romero, Laura Barreiro, Claudio Martínez
    Abstract:

    An enantioselective catalytic vicinal diamination of styrenes is reported, which proceeds under entirely intermolecular reaction control. It relies on a chirally modified aryliodine(I) catalyst and proceeds within an iodine(I/III) manifold with conventional 3-Chloroperbenzoic Acid as a terminal oxidant. An environmentally benign solvent combination not only adds to the attractiveness of the process but also slows down the rate of the undesired background reaction. A total of 30 examples are presented, which consistently provide high enantiomeric excesses in the range 91–98%.

Tetsuro Shinoda – One of the best experts on this subject based on the ideXlab platform.

  • Enantioselective separation of racemic juvenile hormone III by normal-phase high-performance liquid chromatography and preparation of [(2)H(3)]juvenile hormone III as an internal standard for liquid chromatography-mass spectrometry quantification.
    Journal of chromatography. A, 2007
    Co-Authors: Akio Ichikawa, Hiroshi Ono, Kenjiro Furuta, Takahiro Shiotsuki, Tetsuro Shinoda
    Abstract:

    Juvenile hormone III (JH III) racemate was prepared from methyl (2E,6E)-farnesoate via epoxidation with 3-Chloroperbenzoic Acid (mCPBA). Enantioselective separation of JH III was conducted using normal-phase high-performance liquid chromatography (HPLC) on a chiral stationary phase. [(2)H(3)]Methyl (2E,6E)-farnesoate was also prepared from (2E,6E)-farnesoic Acid and [(2)H(4)]methanol (methanol-d(4)) using 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) and 4-dimethylaminopyridine (DMAP); the conjugated double bond underwent isomerization to some degree. Epoxidation of [(2)H(3)]methyl (2E,6E)-farnesoate with mCPBA gave a novel deuterium-substituted internal standard [(2)H(3)]JH III (JH III-d(3)). The standard curve was produced by linear regression using the peak area ratios of JH III and JH III-d(3) in liquid chromatography-mass spectrometry (LC-MS).

  • Enantioselective separation of racemic juvenile hormone III by normal-phase high-performance liquid chromatography and preparation of [2H3]juvenile hormone III as an internal standard for liquid chromatography–mass spectrometry quantification
    Journal of Chromatography A, 2007
    Co-Authors: Akio Ichikawa, Hiroshi Ono, Kenjiro Furuta, Takahiro Shiotsuki, Tetsuro Shinoda
    Abstract:

    Juvenile hormone III (JH III) racemate was prepared from methyl (2E,6E)-farnesoate via epoxidation with 3-Chloroperbenzoic Acid (mCPBA). Enantioselective separation of JH III was conducted using normal-phase high-performance liquid chromatography (HPLC) on a chiral stationary phase. [(2)H(3)]Methyl (2E,6E)-farnesoate was also prepared from (2E,6E)-farnesoic Acid and [(2)H(4)]methanol (methanol-d(4)) using 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) and 4-dimethylaminopyridine (DMAP); the conjugated double bond underwent isomerization to some degree. Epoxidation of [(2)H(3)]methyl (2E,6E)-farnesoate with mCPBA gave a novel deuterium-substituted internal standard [(2)H(3)]JH III (JH III-d(3)). The standard curve was produced by linear regression using the peak area ratios of JH III and JH III-d(3) in liquid chromatography-mass spectrometry (LC-MS).

Giuseppe Cannazza – One of the best experts on this subject based on the ideXlab platform.

  • On the Oxidation of Different Iminic Bonds by Excess of 3-Chloroperbenzoic Acid
    Synlett, 2012
    Co-Authors: Luigino Troisi, Marina Carrozzo, Cinzia Citti, Aurelia Falcicchio, Rosmara Mansueto, Francesca Rosato, Giuseppe Cannazza
    Abstract:

    In the present work the behavior of different substituted iminic bonds toward the oxidative action of 3-Chloroperbenzoic Acid is reported. The C=N bond was or was not oxidized to oxaziridines, amides, oximes, nitroso-, nitro-, and azodioxy compounds depending on the substituents at the iminic group and on the imine/MCPBA stoichiometric ratio