Abstract: The first example of the use of ionic liquids as reaction media in the asymmetric Pd(II)-catalysed oxycarbonylation was investigated. Based on a ligand screening, the chiral box-type ligands were successfully used in the Pd(II)-promoted bicyclisation of pent-4-ene-1,3 diol (±)-1. The kinetic resolution of (±)-1 in the presence of chiral catalyst, p-benzoquinone and acetic acid in ionic liquids under carbon monoxide atmosphere afforded enantioenriched 2,6-dioxabicyclo[3.3.0]octane-3-ones (S,S)-2 (80% ee) and (R,R)-2 (57% ee), respectively.