Supramolecular enantiodifferentiating photoisomerization of (Z)-cyclooctene (1Z) to chiral (E)-isomer (1E) through inclusion and sensitization by 6-O-mono(o-methoxybenzoyl)-β-cyclodextrin (2) was investigated in water and in aqueous methanol solutions at various temperatures. A dramatic inversion of the product chirality was observed to occur by simply changing the solvent from water to methanol. Thus, the supramolecular photosensitization in aqueous solution gave (R)-(-)-1E in 15% enantiomeric excess (ee), whereas in methanol the antipodal (S)-(+)-1E was obtained in 5% ee. The temperature and solvent dependencies of the product ee are discussed.
- Asymmetric synthesis