Organocatalysis

Buckley, Benjamin R.; Neary, Stephen P.

doi:10.1039/b927086h

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Cited by 7 publications

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“…The advent of organocatalysis offers new and insightful strategies for a variety of chemical transformations. − Such strategies offer access to creative molecular syntheses and control of stereochemistry. In addition, there are logistical and cost advantages associated with processes that avoid removal of trace metal residues from transition-metal catalysts.…”

mentioning

confidence: 99%

Metal-Free Transfer Hydrogenation Catalysis by B(C₆F₅)₃

2011

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confidence: 99%

Metal-Free Transfer Hydrogenation Catalysis by B(C₆F₅)₃

2011

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Chiral Ionic Liquid/ESI‐MS Methodology as an Efficient Tool for the Study of Transformations of Supported Organocatalysts: Deactivation Pathways of Jørgensen–Hayashi‐Type Catalysts in Asymmetric Michael Reactions

Maltsev

Chizhov

Zlotin

2011

Chemistry A European J

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The deactivation pathways of Jørgensen-Hayashi-type organocatalysts modified with an ionic liquid fragment in asymmetric Michael reactions of α,β-enals with C- (nitromethane, dimethylmalonate) or N-nucleophiles (N-carbobenzyloxyhydroxylamine) that involved an iminium-ion formation step were studied for the first time by the electrospray ionization mass spectrometry (ESI-MS). "Parasitic" side reactions and undesirable cation intermediates that poisoned the catalysts were identified in accordance with their m/z values as well as their relation to the reported mechanisms of Michael reactions in the presence of O-TMS-α,α-diarylprolinol (TMS=trimethylsilyl) derivatives. The proposed approach may be useful for the study of transformations of other types of organocatalysts modified with ionic groups in various organocatalytic reactions and for the development of novel robust catalysts and processes that would be suitable for large-scale industrial applications.

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