Catalytic asymmetric 1,3-dipolar cycloaddition of nitrile oxides to an achiral allyl alcohol utilizing diisopropyl tartrate as a chiral auxiliary

Article abstract of DOI:10.1246/cl.1996.455

The catalytic asymmetric 1,3-dipolar cycloaddition of nitrile oxides to an achiral allyl alcohol was achieved by the use of a catalytic amount of diisopropyl (R,R)-tartrate as a chiral auxiliary to afford the corresponding (R)-2-isoxazolines with high enantioselectivity. In order to realize reproducible higher stereoselection, the addition of a small amount of ethereal compound such as 1,4-dioxane was crucial.