A mechanochemical desymmetrization of symmetrical bis‐ and tris‐alkynes by a controlled 1,3‐dipolar cycloaddition reaction using nitrile oxide dipoles (NOs). This operationally simple protocol allows access to 3,5‐isoxazole‐alkyne adducts from easily prepared or commercially available symmetrical bis‐ and tris‐alkynes in moderate to excellent yields. In addition, we have highlighted the synthetic utility of 3,5‐isoxazole‐alkyne by developing a route to access, for the first time, β‐ketoenamine‐alkyne derivatives, and unsymmetrical bis‐3,5‐isoxazoles.
A mechanochemical desymmetrization of symmetrical bis- and tris-alkynes via a controlled 1,3-dipolar cycloaddition reaction with nitrile oxide dipoles has been developed. This convenient, efficient, and simple protocol allows access to 3,5-isoxazole-alkyne adducts from easily prepared or commercially available symmetrical bis- and tris-alkynes in moderate to excellent yield. The synthetic utility of 3,5-isoxazole-alkyne was demonstrated by developing a route to access β-ketoenamine-alkyne derivatives and the synthesis of unsymmetrical bis-3,5-isoxazoles products in good to excellent yields.
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