Photosensitized Oxidation of Furans; Part 18: A Simple Method for a One-Pot Synthesis of Functionalized Methyl cis-4-Oxoalk-2-enoates

M. Rosaria Iesce; Flavio Cermola; Alfonso Piazza; Rachele Scarpati; M. Liliana Graziano

doi:10.1055/s-1995-3922

Synthesis 1995; 1995(4): 439-443
DOI: 10.1055/s-1995-3922

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Photosensitized Oxidation of Furans; Part 18: A Simple Method for a One-Pot Synthesis of Functionalized Methyl cis-4-Oxoalk-2-enoates

M. Rosaria Iesce, Flavio Cermola, Alfonso Piazza, Rachele Scarpati^* , M. Liliana Graziano

^*Dipartimento di Chimica Organica e Biologica dell’Università di Napoli Federico II, via Mezzocannone 16, I-80134 Napoli, Italy

Abstract

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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.

2-methoxyfuran sensitized photo-oxygenation - sulfide - methyl cis-4-oxo-2-alkenoate - sulfoxide

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