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- Title
Mechanochemical Desymmetrization of Unbiased Bis‐ and Tris‐alkynes to Access 3,5‐Isoxazoles‐Alkyne Adducts and Unsymmetrical Bis‐3,5‐isoxazoles.
- Authors
Hernandez, Rafael A.; Trakakis, Irini; Do, Jean‐Louis; Cuccia, Louis A.; Friščić, Tomislav; Forgione, Pat
- Abstract
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.
- Subjects
NITRILE oxides; RING formation (Chemistry); MECHANICAL chemistry
- Publication
European Journal of Organic Chemistry, 2023, Vol 26, Issue 29, p1
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202300374