Mr. Iesce et al., PHOTOSENSITIZED OXIDATION OF FURANS .19. STEREOSELECTIVE SYNTHESIS OFFUNCTIONALIZED METHYL CIS 3-AROYL-2,3-EPOXYPROPANOATES VIA ARYL-5-HYDROPEROXY-2,2-DIMETHOXY-2,5-DIHYDROFURANS, Synlett, (11), 1995, pp. 1161
Functionalized methyl cb 3-aroyl-2,3-epoxypropanoates 1 are synthesize
d by singlet oxygen oxygenation of 5-aryl-2-methoxyfurans 2 in methano
l and by base treatment of the resulting crude dihydrofurans 3. Screen
ing experiments revealed that the reaction occurs efficiently only whe
n an electron-withdrawing group is bound at C-4 of 3.