Catalytic Generation of Remote C–N Axial Chirality through Atroposelective<i>de novo</i>Arene Construction
Subhajit Mondal, Santanu Mukherjee
Abstract
The first atroposelective desymmetrization of prochiral N-aryl maleimides through its conversion to axially chiral phthalimides is developed by applying a de novo arene construction strategy. Catalyzed by bis(3,5-dimethylphenyl)prolinol TMS-ether, this reaction proceeds through oxidative [4 + 2]-cycloaddition with α,β-unsaturated aldehydes to generate only a chiral C–N axis remote from the reaction sites with excellent enantioselectivity (up to 97.5:2.5 er).
Topics & Concepts
ChemistryAxial chiralityDesymmetrizationCatalysisCycloadditionEtherArylPhthalimidesChirality (physics)AtropisomerCombinatorial chemistryStereochemistryMedicinal chemistryOrganic chemistryEnantioselective synthesisAlkylChiral symmetry breakingPhysicsPhthalimideQuarkNambu–Jona-Lasinio modelQuantum mechanicsAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralityAsymmetric Synthesis and Catalysis