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<i>De novo</i> synthesis of inherently chiral heteracalix[4]aromatics from enantioselective macrocyclization enabled by chiral phosphoric acid-catalyzed intramolecular S<sub>N</sub>Ar reaction

Xingchi Li, Ying Cheng, Xudong Wang, Shuo Tong, Mei‐Xiang Wang

2024Chemical Science46 citationsDOIOpen Access PDF

Abstract

,O-calix[2]arene[2]triazines from enantioselective macrocyclization enabled by chiral phosphoric acid-catalyzed intramolecular nucleophilic aromatic substitution reaction. In contrast to documented examples, the inherent chirality of the acquired compounds arises from one heteroatom difference in the linking positions of heteracalix[4](het)arenes.

Topics & Concepts

Intramolecular forceEnantioselective synthesisChemistryCatalysisHeteroatomPhosphoric acidChirality (physics)StereochemistryCombinatorial chemistryMedicinal chemistryOrganic chemistryNambu–Jona-Lasinio modelQuarkPhysicsQuantum mechanicsRing (chemistry)Chiral symmetry breakingSupramolecular Chemistry and ComplexesMolecular Sensors and Ion DetectionPorphyrin and Phthalocyanine Chemistry
<i>De novo</i> synthesis of inherently chiral heteracalix[4]aromatics from enantioselective macrocyclization enabled by chiral phosphoric acid-catalyzed intramolecular S<sub>N</sub>Ar reaction | Litcius