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-Nbenzylmaleimide. 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
Atropisomers of arylmaleimides: stereodynamics and absolute configuration / M., Ambrogi; Ciogli, Alessia; M., Mancinelli; S., Ranieri; A., Mazzanti. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - ELETTRONICO. - 78:8(2013), pp. 3709-3719. [10.1021/jo400200v |]
Atropisomers of arylmaleimides: stereodynamics and absolute configuration
CIOGLI, Alessia;
2013
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-Nbenzylmaleimide. 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 spectraFile | Dimensione | Formato | |
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