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Formation and Stability of Prolinol and Prolinol Ether Enamines by NMR: Delicate Selectivity and Reactivity Balances and Parasitic Equilibria

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


Enamine key intermediates in organocatalysis, derived from aldehydes and prolinol or Jørgensen-Hayashitype prolinol ether catalysts, were generated in different solvents and investigated by NMR spectroscopy. Depending on the catalyst structure, trends for their formation and amounts are elucidated. For prolinol catalysts, the first enamine detection in situ is presented and the rapid cyclization ...


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