Spontaneous Resolution of an Achiral Oxime (4‐CLO) into Enantiopure Chiral Crystals and Chirality Induction via Seeding and Alloying

The genesis of homochirality in nature remains a mystery even today. Exploring achiral/prochiral systems can provide valuable insights into the fundamental processes involved in chirality induction and transfer, thereby linking to the evolution of life. Here, we report an achiral 2-(4-chlorophenyl) imidazo[1,2-a]pyrimidine-3-carbaldehydeoxime (4-CLO), which exhibits chirality at the supramolecular level through spontaneous resolution into enantiopure P and M crystals. The strong hydrogen bonding of oxime chains and π-π stacking interactions stabilize the chiral conformation within the tubular architecture and facilitate the emergence of homochirality via helix formation. By utilizing these insights, we demonstrate that the supramolecular chirality could be induced / transferred to two closely related achiral systems (4-IO and 4-HO) via chiral seeding or cocrystallization, resulting in the creation of novel hybrid chiral crystals.