Photodimerization of a novel 2-substituted anthracene linked to a right-handed 3₁₀-helical nonapeptide induced by long-range chiral information transfer from the remote chiral L-Val residue through a chiral domino effect proceeded in a highly regio- and diastereo-differentiating manner to produce the chiral head-to-head anti-photodimer in 90% relative yield with up to 97% diastereomeric excess.