Coupling of Styrylmalonates with Furan and Benzofuran Carbaldehydes: Synthesis and Chemistry of Substituted (4-Oxocyclopent-2-enyl)malonates.

Denis D Borisov, Grigorii R Chermashentsev, Roman A Novikov, Yury V Tomilov

The Journal of organic chemistry 2021 Jun 18

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On the basis of the reaction of β-styrylmalonates with furfural derivatives in the presence of GaCl3 that occurs with opening of the furan ring, an efficient diastereoselective method for the synthesis of trisubstituted cyclopentenones containing a 1,4-diketone moiety was developed. The regularities of the reaction were studied, and a number of chemical reactions of the resulting substrates were carried out. A mechanism for the formation of substituted (4-oxo-2-arylcyclopent-2-enyl)malonates was suggested.

Citation

Denis D Borisov, Grigorii R Chermashentsev, Roman A Novikov, Yury V Tomilov. Coupling of Styrylmalonates with Furan and Benzofuran Carbaldehydes: Synthesis and Chemistry of Substituted (4-Oxocyclopent-2-enyl)malonates. The Journal of organic chemistry. 2021 Jun 18;86(12):8489-8499