title: Atropisomers of arylmaleimides: stereodynamics and absolute configuration.
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.
authors.affiliation: Department of Industrial Chemistry Toso Montanari, University of Bologna, Viale Risorgimento 4, 40136-Bologna, Italy.
authors.forename: Martina
authors.initials: M
authors.lastname: Ambrogi
authors.forename: Alessia
authors.initials: A
authors.lastname: Ciogli
authors.forename: Michele
authors.initials: M
authors.lastname: Mancinelli
authors.forename: Silvia
authors.initials: S
authors.lastname: Ranieri
authors.forename: Andrea
authors.initials: A
authors.lastname: Mazzanti