An Efficient and User-Friendly Strategy for the Synthesis of Cyclopropane and Dihydrofuran Rings from Difunctional Compounds

Abstract

K₂CO₃-NaHCO₃-mediated conjugate-addition-initiated ring-closure (CAIRC) reaction of various active methylene compounds to 2-bromo-2-cyclopentenone in the presence of [BMIM]PF₆-H₂O (2:1) producing carbocyclic and heterocyclic compounds is described. The use of [BMIM]PF₆-H₂O as a solvent for CAIRC reaction is advantageous offering simple product isolation and shorter reaction times compared to conventional solvents. This reaction system can provide a general and practical method for the construction of 2,2-disubstituted cyclopropanes and polycyclic dihydrofuran derivatives containing electron-deficient substituents.

Key words

ionic liquids - β-dicarbonyl compounds - dihydrofurans - cyclopropanation - conjugate-addition-initiated ring-closure reaction

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