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NMR Investigations on the Proline-Catalyzed Aldehyde Self-Condensation: Mannich Mechanism, Dienamine Detection, and Erosion of the Aldol Addition Selectivity

Schmid, M. B. ; Zeitler, K. ; Gschwind, Ruth M.



Abstract

The proline-catalyzed self-condensation of aliphatic aldehydes in DMSO with varying amounts of catalyst was studied by in situ NMR spectroscopy. The reaction profiles and intermediates observed as well as deuteration studies reveal that the proline-catalyzed aldol addition and condensation are competing, but not consecutive, reaction pathways. In addition, the rate-determining step of the ...

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