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 observations of accelerating reaction rate in both the alpha-aminooxylation and alpha-amination reactions.
Iwamura
Hiroshi
H
Department of Chemistry, Imperial College, London SW7 2AZ, United Kingdom.
Wells
David H
DH
Mathew
Suju P
SP
Klussmann
Martin
M
Armstrong
Alan
A
Blackmond
Donna G
DG
D000447:Aldehydes / Q000737:chemistry*; D000586:Amination; D002384:Catalysis; D006860:Hydrogen Bonding; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D023303:Oxazolidinones / Q000737:chemistry; D011392:Proline / Q000737:chemistry*
D000447:Aldehydes; D023303:Oxazolidinones; D011392:Proline