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9.9.1.1.1.2.5 Method 5: From 1,3-Dicarbonyl Compounds and 1-Nitroalk-1-enes

DOI: 10.1055/sos-SD-009-00244

König, B.Science of Synthesis, (20019195.

Michael addition of 1,3-dicarbonyl compounds 54 to nitroalkenes 53 with subsequent cyclization and loss of nitric acid yields furans 55 (Scheme 19).[‌135‌‌139‌] Similar reactions have been reported with alkenyl sulfoxides.[‌140‌] With cyclic 1-nitroalk-1-enes, 4,5-annulated alkyl 2-alkyl-3-furoates are obtained.[‌141‌] In the reaction either the sodium salt of the dicarbonyl compounds is used, or potassium fluoride or piperidine is added.

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