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Kinetic resolution of Pent-4-ene-1,3-diol by Pd(II)-catalysed Oxycarbonylation in Ionic Liquids
1 , * 2 , 1 , 1 , 2
1  Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, SK-812 37 Bratislava, Slovakia,
2  University Paris-Sud 11, ICMMO, Orsay Cedex France

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.
Keywords: Kinetic resolution, oxycarbonylation, chiral ligand, asymmetric catalysis, ionic liquids.