Asymmetric 1,3-Dipolar Cycloaddition of Nitrile Oxides to γ-Substituted Allylic Alcohols
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The asymmetric 1,3-dipolar cycloaddition of nitrile oxides to γ-substituted allylic alcohols was achieved by the use of diisopropyl (R,R)-tartrate as a chiral auxiliary to afford the corresponding 3,4,5-trisubstituted-2-isoxazolines with high regio- and enantioselectivities. 4,5-trans-2-Isoxazolines derived from ethyl (E)-4-hydroxy-2-butenoate were transformed to the corresponding 4,5-cis-2-isoxazolines by the treatment with a base through isomerization and lactonization.
- Chemistry Letters
Chemistry Letters 1998(10), 1023-1024, 1998-10-05
The Chemical Society of Japan