Asymmetric intramolecular Pd(II)-catalysed oxycarbonylation of alkene-1,3-diols

Abstract

The first example of asymmetric oxycarbonylative bicyclisation of racemic pent-4-ene-1,3-diol (±)-1 catalysed by palladium(II) with chiral bis(oxazoline) ligands was investigated. The kinetic resolution of (±)-1 in the presence of chiral catalyst, p-benzoquinone in acetic acid under carbon monoxide atmosphere (balloon) afforded both optically enriched 2,6-dioxabicyclo[3.3.0]octan-3-ones (R,R)-2 and (S,S)-2, respectively. ©ARKAT USA, Inc.