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Catalytic Generation of Remote C-N Axial Chirality through Atroposelective de novo Arene Construction
Subhajit Mondal1, Santanu Mukherjee1
1Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India.
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).
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