Kinetic and Stereochemical Evidence for the Involvement of Only One Proline 
Molecule in the Transition States of Proline-Catalyzed Intra- and 
Intermolecular Aldol Reactions

Hoang, Linh; Bahmanyar, S.; Houk, K. N.; List, Benjamin

doi:10.1021/ja028634o

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Kinetic and Stereochemical Evidence for the Involvement of Only One Proline Molecule in the Transition States of Proline-Catalyzed Intra- and Intermolecular Aldol Reactions

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Hoang, L., Bahmanyar, S., Houk, K. N., & List, B. (2003). Kinetic and Stereochemical Evidence for the Involvement of Only One Proline Molecule in the Transition States of Proline-Catalyzed Intra- and Intermolecular Aldol Reactions. Journal of the American Chemical Society, 125(1), 16-17. doi:10.1021/ja028634o.

Zitierlink: https://hdl.handle.net/11858/00-001M-0000-0014-A4C9-3

Zusammenfassung

Contrary to the widely accepted mechanism of the Hajos−Parrish−Eder−Sauer−Wiechert reaction, we have obtained evidence for the involvement of only one proline molecule in the transition states of both inter- and intramolecular aldol reactions. Our conclusions are based on kinetic measurements and the absence of nonlinear and dilution effects on the asymmetric catalysis, and are supported by B3LYP/6-31G* calculations. Complementary to recent theoretical studies, our results provide the foundation of a unified enamine catalysis mechanism of proline-catalyzed inter- and intramolecular aldol reactions.