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

• Published in: Journal of physical organic chemistry Vol. 25; no. 6; pp. 515 - 522
• Main Authors: Miranda, Margarida S., Rodríguez-Borges, José E., Esteves da Silva, Joaquim C. G., García-Mera, Xerardo
• Format: Journal Article
• Language: English
• Published: Chichester, UK John Wiley & Sons, Ltd 01.06.2012
• Subjects: density functional theory; exo-selectivity; ionic aza-Diels-Alder reactions; protonated quiral glyoxylate imines; transition states
• ISSN: 0894-3230; 1099-1395
• DOI: 10.1002/poc.1949

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, Lee–Yang–Parr 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‐Diels–Alder reactions. Copyright © 2011 John Wiley & Sons, Ltd. 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, Lee–Yang–Parr 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‐Diels–Alder reactions.