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DOI: 10.1055/s-2006-926459
An Efficient and User-Friendly Strategy for the Synthesis of Cyclopropane and Dihydrofuran Rings from Difunctional Compounds
Publication History
Publication Date:
27 April 2006 (online)
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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