A facile synthesis of stable β-amino-N-/O-hemiacetals through a catalyst-free three-component Mannich-type reaction
Castillo, Juan C.
D'Vries, Richard F.
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A practical, straightforward and one-step procedure for the synthesis of novel and stable b-amino-N-/Ohemiacetals (i.e. c-aminoalcohols) is provided. The title compounds were obtained in good to excellent yields through an uncatalyzed three-component reaction by treatment of secondary amines with polyformaldehyde and electron-rich alkenes in acetonitrile as solvent at ambient temperature. The reactions proceeded with the formation of iminium ions, through a Mannich-type reaction, as the key intermediates for the generation of the target products. Single crystal X-ray analysis of derivative 4l confirmed unequivocally the structure and stability of the obtained compounds.