Stereoselectivity of the aza-Diels-Alder reaction between cyclopentadiene and protonated phenylethylimine derived from glyoxylates. A density functional theory study

• Type: Article in International Scientific Journal
• Date: 2009

Authors

Filipe Teixeira (Author) Other; Jose E Rodriguez Borges (Author) FCUP; Andre Melo (Author) FCUP; Natalia N D S Cordeiro (Author) FCUP

Journal

Title: Chemical Physics Letters

Vol. 477

Pages: 60-64

ISSN: 0009-2614

Publisher: Elsevier

Indexing

ISI Web of Knowledge - 15 Citations

Scopus - 14 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

Other information

Authenticus ID: P-003-HEE

DOI: 10.1016/j.cplett.2009.06.009

Abstract (EN): The aza-Diels-Alder reaction of cyclopentadiene with protonated (S)-phenylethylimine of methyl carboxilate was studied using density functional theory (DFT) at the B3LYP/6-31G(d) level to elucidate the reported stereoselectivity of this reaction. Four independent reaction pathways were found, all of them proceeding through a concerted, asynchronous, mechanism. Inclusion of solvent effects revealed a high exo/endo stereoselectivity that decreases with increasing temperature, in good accordance with the experimental reports. (c) 2009 Published by Elsevier B.V.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 5