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Synlett 1995; 1995(11): 1161-1162
DOI: 10.1055/s-1995-5208
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Photosensitized Oxidation of Furans. 19.1 Stereoselective Synthesis of Functionalized Methyl cis 3-Aroyl-2,3-epoxypropanoates via 5-Aryl-5-hydroperoxy-2,2-dimethoxy-2,5-dihydrofurans

M. R. Iesce, F. Cermola, A. Guitto, R. Scarpati* , M. L. Graziano
  • *Dipartimento di Chimica Organica e Biologica dell’Università di Napoli Federico II, via Mezzocannone 16, I-80134 Napoli, Italy
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Publication Date:
31 December 2000 (online)

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Functionalized methyl cis 3-aroyl-2,3-epoxypropanoates 1 are synthesized by singlet oxygen oxygenation of 5-aryl-2-methoxyfurans 2 in methanol and by base treatment of the resulting crude dihydrofurans 3. Screening experiments revealed that the reaction occurs efficiently only when an electron-withdrawing group is bound at C-4 of 3.

Stereoselective epoxidation - methyl cis 3-aroyl-2,3-epoxypropanoates - 5-hydroperoxy-2,5-dihydrofurans - 2-alkoxyfurans - photosensitized oxidation