Selective and efficient transformation of N-(4-substituted benzoyl)-α-dehydroarylalanine alkyl esters into 4,5-dihydrooxazole derivatives via photoinduced electron transfer

The irradiation of N-(4-substituted benzoyl)-α-dehydroarylalanine alkyl esters (1) in methanol containing triethylamine (TEA) was found to quantitatively give cis- and trans-4,5-dihydrooxazole derivatives (2), which were described as being formed via electron transfer from TEA to the excited-state (E)-1 followed by kinetically-controlled cyclization of the (E)-1-derived anion radical. A product composition analysis showed that the cis-2/trans-2 composition ratio is greatly varied depending on the stereoelectronic properties of the substituents, the polarity of protic solvents and the concentration of TEA.