Self-Assembly of Molecules in Crystal and Its Application to Selective Organic Synthesis

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It was found that self-assembly of molecules in crystal is not always adequate for a selective reaction. However, we found that when molecules of reactant are assembled together with host molecules, the former are arranged regularly and the solid state reaction proceeds selectively.For example, photoirradiation of a 1 : 1 inclusion complex powder of N-benzoylmethyl-delta-valerolactam (2) and the optically active host (1) which had been derived from tartaric acid, in a water suspension under stirring gave optically almost pure bicyclic delta-valerolactam alcohol. X-ray crystal structure analysis of the inclusion complex showed that molecules of 2 and 1 are self-assembled to form 1 : 1 inclusion complex in which precise chiral recognition occurs. According to the chiral recognition, attack of reagent from the front and rear side of the reactant is controlled and single product is obtained. Inclusion crystals of various derivatives of 2 with 1 were also prepared and their photoreactions gave optically pure photocyclization products.