Asymmetric intramolecular Pd(II)-catalysed amidocarbonylation of unsaturated amino alcohols

The first example of an asymmetric carbonylative bicyclisation of racemic N-protected 1-amino-pent-4-ene-3-ols (±)-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 afforded enantiomerically enriched derivatives of 2-oxa-6-azabicyclo[3.3.0]octan-3-ones (R,R)-2 and (S,S)-2, respectively.