Enantiospecific Generation and Trapping Reactions of Aryne Atropisomers
Yun‐Long Wei, Guillaume Dauvergne, Jean Rodriguez, Yoann Coquerel
Abstract
Enantioenriched aryne atropisomers having a biaryl stereogenic axis vicinal to the reactive triple bond are demonstrated to exist. These reaction intermediates are easily produced in situ and can undergo the standard aryne cycloaddition chemistry in an enantiospecific manner. Notably, the aryne atropisomers herein have allowed the practical syntheses of a small nanographene as well as some triptycene and anthracene derivatives that embed stereogenic axes of controlled absolute configurations.
Topics & Concepts
AryneAtropisomerStereocenterChemistryVicinalAnthraceneCycloadditionStereochemistryOrganic chemistryEnantioselective synthesisCatalysisCyclization and Aryne ChemistrySynthesis and Properties of Aromatic CompoundsAxial and Atropisomeric Chirality Synthesis