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.
M. Ambrogi, A. Ciogli, M. Mancinelli, S. Ranieri, A. Mazzanti (2013). Atropisomers of arylmaleimides: Stereodynamics and absolute configuration. JOURNAL OF ORGANIC CHEMISTRY, 78(8), 3709-3719 [10.1021/jo400200v].
Atropisomers of arylmaleimides: Stereodynamics and absolute configuration
MANCINELLI, MICHELE;RANIERI, SILVIA;MAZZANTI, ANDREA
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-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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
