Organocatalytic Asymmetric Conjugate Addition of Aldehydes to Nitroolefins: Identification of Catalytic Intermediates and the Stereoselectivity-Determining Step by ESI-MS

Organocatalytic Asymmetric Conjugate Addition of Aldehydes to Nitroolefins: Identification of Catalytic Intermediates and the Stereoselectivity-Determining Step by ESI-MS

Looking back: The asymmetric organocatalytic 1,4‐addition of aldehydes to nitroolefins was studied by ESI‐MS. Analysis of the back reaction starting from quasienantiomeric mass‐labeled 1,4‐adducts (see scheme) provided conclusive evidence for an enamine rather than an enol mechanism, and allowed ide...

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Veröffentlicht in:Angewandte Chemie International Edition 2013-11, Vol.52 (48), p.12619-12623
Hauptverfasser: Bächle, Florian, Duschmalé, Jörg, Ebner, Christian, Pfaltz, Andreas, Wennemers, Helma
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes
asymmetric catalysis
Asymmetry
Catalysis
Catalysts
Conjugates
mass spectrometry
organocatalysis
peptides
reaction mechanisms
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Beschreibung
Zusammenfassung:Looking back: The asymmetric organocatalytic 1,4‐addition of aldehydes to nitroolefins was studied by ESI‐MS. Analysis of the back reaction starting from quasienantiomeric mass‐labeled 1,4‐adducts (see scheme) provided conclusive evidence for an enamine rather than an enol mechanism, and allowed identification of the enantioselectivity‐determining step.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201305338