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Organo-and BiocatalysisKey words aza-Michael addition piperidines quinine-derived primary diamines quinine-derived tertiary diamines Significance: Chen, Fan and colleagues developed an intramolecular aza-Michael addition of carbamate-protected amines to enones. The reaction is catalyzed by the combination of the quinine-derived primary/tertiary diamine and trifluoroacetic acid (TFA). The authors present a transitionstate model, which includes imine activation of the enone, hydrogen bonding of the protonated tertiary amine to the electron-rich carbamate oxygen, and the minimization of steric interactions. Finally, the presented method is of value for the synthesis of key intermediates towards natural products.
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