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 spectra
2013
arylmaleimides; stereodynamics; absolute configuration
01 Pubblicazione su rivista::01a Articolo in rivista
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 |]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/514844
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