Atroposelective synthesis of -disubstituted []paracyclophanes is a difficult task in organic chemistry. We describe a facile approach for the synthesis of -disubstituted []paracyclophanes using Pd-catalyzed enantioselective C-H olefination and sequential reductive cleavage. A wide range of []paracyclophanes was obtained with excellent enantioselectivity. Thermodynamic analysis revealed that the rotational barrier of -disubstituted []paracyclophanes was lower than that of -disubstituted []paracyclophanes. The synthesized planar-chiral [14]paracyclophane showed a bright fluorescence emission and impressive circularly polarized luminescence activity.
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An Approach for Highly Enantioselective Synthesis of -Disubstituted []Paracyclophanes.
J Org Chem
October 2024
Key Laboratory of Radiopharmaceuticals, Ministry of Education, College of Chemistry, Beijing Normal University, Beijing 100875, China.
Atroposelective synthesis of -disubstituted []paracyclophanes is a difficult task in organic chemistry. We describe a facile approach for the synthesis of -disubstituted []paracyclophanes using Pd-catalyzed enantioselective C-H olefination and sequential reductive cleavage. A wide range of []paracyclophanes was obtained with excellent enantioselectivity.
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