Affiliation:
1. Department of Chemistry Korea Advanced Institute of Science and Technology (KAIST) Daejeon 34141 Korea
2. Brain Science Institute Korea Institute of Science and Technology Seoul 02792 Korea
3. Division of Bio-Medical Science & Technology KIST School University of Science and Technology Seoul 02792 Korea
Abstract
AbstractIn this study, we focused on the synthesis of tetraazamacrocycles, an essential class of macrocyclic compounds with applications in coordination chemistry, pharmaceuticals, and catalysis. To accomplish this, we developed a ligand‐controlled palladium‐catalyzed allylic substitution approach using bicyclic bridgehead phosphoramidite (briphos) ligands. This approach allowed us to selectively achieve [1+1] and [1+2] allylic aminations between allylic diols and diamines, while avoiding the formation of cyclic [1+1] products. By combining this approach with sequential acetylation and allylic amination, we successfully synthesized tetraazamacrocycles with ring sizes ranging from 16 to 38. These findings demonstrate the potential of a sequential allylation strategy for synthesizing complex molecules with broad applications in the fields of chemistry, pharmaceuticals, and medicine.
Funder
National Research Foundation of Korea
Korea Advanced Institute of Science and Technology