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Updated: May 13, 2026

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Published on: June 13, 2022
Atropisomers of arylmaleimides: stereodynamics and absolute configuration
Martina Ambrogi1, Alessia Ciogli, Michele Mancinelli
1Department of Industrial Chemistry Toso Montanari, University of Bologna, Viale Risorgimento 4, 40136-Bologna, Italy.
Abstract:
4-Aryl-3-bromo-N-benzylmaleimides and 3,4-biaryl-N-benzylmaleimides have been synthesized by a modified Suzuki cross-coupling reaction from 3,4-dibromo-N-benzylmaleimide. The conformational studies by dynamic NMR and DFT calculations showed that the interconversion barrier between the two available skewed conformations is under steric control. When the aryl group was a 2-methylnaphthyl, thermally stable atropisomers were isolated by enantioselective HPLC and their absolute configurations were assigned by TD-DFT simulations of the ECD spectra.
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