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The supramolecular strategy was subjected to the asymmetric hydrogenation of 4-methylumbelliferone by electrochemical reduction in the presence of a chiral macrocyclic multifarane [3,3], which offered a L-7-hydroxy-4-methylchroman-2-one product with a chemical yield of 65% and enantioselectivity up to >99% ee. The high stability of the developed chiral supramolecular electrode guaranteed the recyclability and repeatability in the electrolysis, and therefore, the application was extended to more coumarin derivatives to provide satisfactory chemical yields and enantioselectivities.