PHOTOSENSITIZED OXIDATION OF FURANS .18. A SIMPLE METHOD FOR A ONE-POT SYNTHESIS OF FUNCTIONALIZED METHYL CIS-4-OXOALK-2-ENOATES

Authors
IESCE MR CERMOLA F PIAZZA A SCARPATI R GRAZIANO ML
Citation
Mr. Iesce et al., PHOTOSENSITIZED OXIDATION OF FURANS .18. A SIMPLE METHOD FOR A ONE-POT SYNTHESIS OF FUNCTIONALIZED METHYL CIS-4-OXOALK-2-ENOATES, Synthesis, (4), 1995, pp. 439-443
Citations number
33
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
4
Year of publication
1995
Pages
439 - 443
Database
ISI
SICI code
0039-7881(1995):4<439:POOF.A>2.0.ZU;2-4
Abstract
Functionalized methyl cis-4-oxoalk-2-enoates 2 are synthesized in a on e-pot procedure by singlet oxygen oxygenation of the corresponding 2-m ethoxyfurans 1 in methanol and reduction of the resulting hydroperoxid es 4 and 5 by the sulfides 6 which are selectively oxidized into the s ulfoxides 7. The synthetic method has a wide range of applicability an d affords compounds 2 stereoselectively and in good yields; concomitan tly the sulfoxides 7 are obtained in excellent yields.