A Novel Absolute Asymmetric Synthesis Using Photoracemization and Preferential Crystallization

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When a solution of an achiral substrate was irradiated, a crystalline photodimer was precipitated as an optical active form according to the progress of the dimerization reaction. A new absolute asymmetry synthesis was developed. This phenomenon depends on the stereoselective formation of C2 chiral photodimer, the conglomerate property of the crystal, and the apparent racemization of the dimer by the back reaction. We achieved the asymmetric synthesis in 50%ee by the use of sun light and in 80%ee with the UV lamp.