Mixing of powdered chiral hosts and achiral N,N-dialkylphenylglyoxylamide guest compounds gives inclusion complexes in which the latter molecules are arranged in a chiral form, although such complexes are not obtained by recrystallisation: the chirality of the guest compounds are frozen by photoreaction which gives optically active P-lactams and oxazolidinones.
The steric course of the photocyclization reaction of the title achiral compounds (1) to optically active trans-dihydrofuran derivatives (2) was controlled by carrying out the reaction in inclusion crystals (4) with optically active hosts (3) derived from tartaric acid. The mechanism of the enantioselective reaction of 1 in 4 was studied by X-ray structural analysis of 4. In some cases, the steric course of the photoreaction was different depending on whether 4 was prepared by recrystallization or by mixing of 1 and 3.
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