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

• Tipo: Artigo em Revista Científica Internacional
• Data: 2009

Autores

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

Revista

Título: Chemical Physics Letters

Vol. 477

Páginas: 60-64

ISSN: 0009-2614

Editora: Elsevier

Indexação

ISI Web of Knowledge - 15 Citações

Scopus - 14 Citações

Classificação Científica

FOS: Ciências exactas e naturais > Química

Outras Informações

ID Authenticus: 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.

Idioma: Inglês

Tipo (Avaliação Docente): Científica

Nº de páginas: 5