The study of chirogenesis of organic molecules is important to elucidate the origin of the homochirality of biomolecules on Earth. Here, we have accomplished chiral symmetry breaking from a racemate using optical vortices with orbital angular momentum and a helical wavefront. We propose a new methodology of asymmetric transformation by the combination of enantioselective crystal nucleation by irradiation with optical vortices and crystallization-induced dynamic optical resolution of conglomerate crystals. Chiral green vortices generated using a spiral phase plate (SPP) with a 532 nm CW-laser were used to irradiate a supersaturated solution of a racemic isoindolinone, leading to crystal nucleation. The handedness of the crystals were controlled by the winding direction of the chiral optical vortices. The molecular chirality of the isoindolinone was then amplified by dynamic crystallization.

A new type of oxidative Se-dealkylation reaction was found in either the reaction of 1,8-bis(methylseleno)naphthalene and naphtho[1,8-b,c]-1,5-diselenocin with benzoyl peroxide or the reaction of their Se-oxides with carboxylic acid anhydrides.

Dynamic enantioselective crystallization enabled the chiral symmetry breaking of two spiropyrans and one spirooxazine. The three spiro compounds afforded racemic conglomerate crystals, and easily racemized in alcoholic solution without irradiation. Optically pure enantiomorphic crystals were obtained by vapor‐diffusion crystallization or attrition‐enhanced deracemization (Viedma ripening). Their absolute configurations were determined by single‐crystal X‐ray analysis and each enantiomorphic crystal was correlated with its solid‐state circular dichroism (CD) spectrum.

The reaction of N-cinnamoylthioureas with DBU proceeded in an unprecedented “umpolung” cyclization fashion to give five-membered iminothiazolidinones and/or thiohydantoins.

The study of chirogenesis of organic molecules is important to elucidate the origin of the homochirality of biomolecules on Earth. Here, we have accomplished chiral symmetry breaking from a racemate using optical vortices with orbital angular momentum and a helical wavefront. We propose a new methodology of asymmetric transformation by the combination of enantioselective crystal nucleation by irradiation with optical vortices and crystallization-induced dynamic optical resolution of conglomerate crystals. Chiral green vortices generated using a spiral phase plate (SPP) with a 532 nm CW-laser were used to irradiate a supersaturated solution of a racemic isoindolinone, leading to crystal nucleation. The handedness of the crystals were controlled by the winding direction of the chiral optical vortices. The molecular chirality of the isoindolinone was then amplified by dynamic crystallization.