Photosensitized oxidation of furans; Part 18: A simple method for a one-pot synthesis of functionalized methyl cis-4-oxoalk-2-enoates

Article abstract of DOI:10.1055/s-1995-3922

Functionalized methyl cis-4-oxoalk-2-enoates 2 are synthesized in a one-pot procedure by singlet oxygen oxygenation of the corresponding 2-methoxyfurans 1 in methanol and reduction of the resulting hydroperoxides 4 and 5 by the sulfides 6 which are selectively oxidized into the sulfoxides 7. The synthetic method has a wide range of applicability and affords compounds 2 stereoselectively and in good yields; concomitantly the sulfoxides 7 are obtained in excellent yields.