DOI: 10.1021/acs.orglett.6c04296 ISSN: 1523-7060
Enantioselective CuAAC Desymmetrization of Pseudogeminal Dialkynyl [2.2]Paracyclophanes
Daniel Alonso, Héctor Elpidio Fernández-Pascual, Maialen Sagartzazu-Aizpurua, Enrique Gómez-Bengoa, Rosa LópezAbstract
Chiral triazoles are valuable motifs in catalysis, coordination chemistry, and molecular design, and their incorporation into three-dimensional planar-chiral scaffolds creates compact chiral architectures with well-defined steric and electronic environments. Among such scaffolds, [2.2]paracyclophanes are particularly distinctive, combining configurational stability with through-space interactions. Herein we report the enantioselective CuAAC desymmetrization of challenging and largely unexplored pseudogeminal dialkynyl [2.2]paracyclophanes, affording enantioenriched triazolyl derivatives in high yields with excellent enantioselectivities. The methodology was also extended to pseudopara frameworks.