Two-Step Asymmetric Reaction Using the Frozen Chirality Generated by Spontaneous Crystallization

N,N-Diallyl-4-methyl-1-propyl-2-quinolone-3-carboxamide afforded chiral crystals of a P2₁ crystal system by spontaneous crystallization. The molecular chirality in the crystal was retained after the crystals were dissolved in a solvent at a low temperature, and the frozen molecular chirality was effectively transferred to the products by a two-step reaction involving hydrogenation and intermolecular photocycloaddition reactions.