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.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 3934-3937 |
| Number of pages | 4 |
| Journal | Bioorganic and Medicinal Chemistry Letters |
| Volume | 19 |
| Issue number | 14 |
| DOIs | |
| State | Published - Jul 15 2009 |
Keywords
- Asymmetric catalysis
- Kinetics
- Mechanism
- Organocatalysis
- Proline
ASJC Scopus subject areas
- Biochemistry
- Molecular Medicine
- Molecular Biology
- Pharmaceutical Science
- Drug Discovery
- Clinical Biochemistry
- Organic Chemistry
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Cite this
Zotova, N., Broadbelt, L. J., Armstrong, A., & Blackmond, D. G. (2009). Kinetic and mechanistic studies of proline-mediated direct intermolecular aldol reactions. Bioorganic and Medicinal Chemistry Letters, 19(14), 3934-3937. https://doi.org/10.1016/j.bmcl.2009.03.112