Affiliation:
1. Department of Chemistry and Biochemistry Concordia University 7141 rue Sherbrooke O. Montreal QC, H4B 1R6 Canada
2. School of Chemistry University of Birmingham Edgbaston Birmingham B15 2TT UK
Abstract
AbstractA 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.
Subject
Organic Chemistry,Physical and Theoretical Chemistry