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

• Type: Article in International Scientific Journal
• Date: 2012

Authors

Margarida S Miranda (Author) FCUP; Jose Rodriguez Borges (Author) FCUP; Joaquim C G E Esteves da Silva (Author) FCUP; Xerardo Garcia Mera (Author) Other

Journal

Title: Journal of Physical Organic Chemistry

Vol. 25

Pages: 515-522

ISSN: 0894-3230

Publisher: Wiley-Blackwell

Indexing

ISI Web of Knowledge - 4 Citations

Scopus - 5 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

Other information

Authenticus ID: P-002-9R5

DOI: 10.1002/poc.1949

Abstract (EN): 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. Copyright (c) 2011 John Wiley & Sons, Ltd.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 8