Atropisomers of Arylmaleimides: Stereodynamics and Absolute Configuration

作者:Ambrogi Martina; Ciogli Alessia; Mancinelli Michele; Ranieri Silvia; Mazzanti Andrea*
来源:Journal of Organic Chemistry, 2013, 78(8): 3709-3719.
DOI:10.1021/jo400200v

摘要

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.

  • 出版日期2013-4-19