The homochirality of life remains an unresolved scientific question. Prevailing models postulate that homochirality arose through mutual antagonism. In this mechanism, molecules of opposite handedness deactivate each other, amplifying even a small enantiomeric excess into a larger proportion. In this paper, we present chiral molecular clips that replicate this process. Through π–π stacking and complementary hydrogen bonds, shape-persistent clips of opposite chirality bind to each other more strongly than those of the same chirality, resulting in chiral amplification. This process was studied quantitatively, revealing a remarkably high degree (180-fold) of stereoselection, unmatched by any non-covalent assemblies reported to date. We demonstrate how this symmetry-breaking, in conjunction with the chiral composition of the host, impacts the binding of nonchiral molecules. Our findings illustrate how chirality transfer and amplification occur non-covalently from hosts to guests, offering insights into the evolutionary origins of homochirality in life’s molecular building blocks.

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