Kinetic and mechanistic studies of proline-mediated direct intermolecular aldol reactions |
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| Authors: | Natalia Zotova Linda J Broadbelt Alan Armstrong Donna G Blackmond |
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| Institution: | 1. Department of Chemical Engineering and Chemical Technology, Imperial College, London SW7 2AZ, United Kingdom;2. Department of Chemistry, Imperial College, London SW7 2AZ, United Kingdom |
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| Abstract: | 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. |
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