Catalytic Asymmetric 1, 3-Dipolar Cycloaddition of Nitrile Oxides to an Achiral Allyl Alcohol Utilizing Diisopropyl Tartrate as a Chiral Auxiliary
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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 (<I>R</I>,<I>R</I>)-tartrate as a chiral auxiliary to afford the corresponding (<I>R</I>)-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.
- Chemistry Letters
Chemistry Letters 1996(6), 455-456, 1996-06
The Chemical Society of Japan