Probing the Active Catalyst in Product-Accelerated Proline-Mediated Reactions

Probing the Active Catalyst in Product-Accelerated Proline-Mediated Reactions

A new catalytic cycle involving only soluble proline complexes or adducts is proposed for the reactions in eq 1 based on kinetic observations and molecular modeling studies. This reaction pathway circumventing free proline and incorporating hydrogen-bonded reaction product helps to rationalize the o...

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Veröffentlicht in:Journal of the American Chemical Society 2004-12, Vol.126 (50), p.16312-16313
Hauptverfasser: Iwamura, Hiroshi, Wells, David H, Mathew, Suju P, Klussmann, Martin, Armstrong, Alan, Blackmond, Donna G
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes - chemistry
Amination
Catalysis
Chemistry
Exact sciences and technology
Hydrogen Bonding
Kinetics
Kinetics and mechanisms
Magnetic Resonance Spectroscopy
Models, Molecular
Organic chemistry
Oxazolidinones - chemistry
Proline - chemistry
Reactivity and mechanisms
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Beschreibung
Zusammenfassung:A new catalytic cycle involving only soluble proline complexes or adducts is proposed for the reactions in eq 1 based on kinetic observations and molecular modeling studies. This reaction pathway circumventing free proline and incorporating hydrogen-bonded reaction product helps to rationalize the observations of accelerating reaction rate in both the α-aminooxylation and α-amination reactions.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja0444177