Kinetic and mechanistic studies of proline-mediated direct intermolecular aldol reactions.
Reaction progress kinetic analysis of the proline-mediated intermolecular aldol reaction shows that the rate depends on the concentrations of both the donor ketone1 and the electrophilic aldehyde 2, implying that enamine formation cannot be rate-determining. The observed kinetics and deuterium isotope effects are consistent with formation of the product iminium species as the rate-determining step.
Department of Chemical Engineering and Chemical Technology, Imperial College, London, United Kingdom.
Natalia
N
Zotova
Linda J
LJ
Broadbelt
Alan
A
Armstrong
Donna G
DG
Blackmond
D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D003903:Deuterium / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D007700:Kinetics; D011392:Proline / Q000737:chemistry*
D000447:Aldehydes; D007659:Ketones; D011392:Proline; D003903:Deuterium