Aza-Diels-Alder reaction between cyclopentadiene and protonated N-phenylethyliminoacetates of 8-phenylmenthol and 8-phenylneomenthol: a density functional theory study

作者：Miranda Margarida S^*; Rodriguez Borges Jose; Esteves da Silva Joaquim C G; Garcia Mera Xerardo

来源：Journal of Physical Organic Chemistry, 2012, 25(6): 515-522.

DOI：10.1002/poc.1949

• density functional theory
• exo-selectivity
• ionic aza-Diels-Alder reactions
• protonated quiral glyoxylate imines
• transition states

The cycloaddition between glyoxylate imines possessing two chiral auxiliaries, N-(R)- or N-(S)-1-phenylethyl and 8-phenylmenthyl or 8-phenylneomenthyl, and cyclopentadiene is described. Computational calculations using density functional theory with the Becke, three-parameter, LeeYangParr functional and the 6-31G(d) basis set were performed to better understand the highly diastereoselective mechanism and the exo-selectivity observed experimentally for these ionic aza-DielsAlder reactions.

• 出版日期2012-6