1,3-versus 1,4-[(pi)4+(pi)2] Cycloadditions between methyl glyoxylate oxime and cyclopentadiene or cyclopentene

• Tipo: Artigo em Revista Científica Internacional
• Data: 2012

Autores

Carlos A D Sousa (Autor) Outra; Luisa L C Vale (Autor) FCUP; Xerardo Garcia Mera (Autor) Outra; Jose E Rodriguez Borges (Autor) FCUP

Revista

Título: Tetrahedron

Vol. 68

Páginas: 1682-1687

ISSN: 0040-4020

Editora: Elsevier

Indexação

ISI Web of Knowledge - 17 Citações

Scopus - 18 Citações

Classificação Científica

FOS: Ciências exactas e naturais > Química

Outras Informações

ID Authenticus: P-002-D2C

DOI: 10.1016/j.tet.2011.12.073

Abstract (EN): The acid catalyzed cycloaddition reaction of methyl glyoxylate oxime with cyclopentadiene (CPD) afforded the corresponding aza-Diels-Alder adducts, the endo and exo isomers of (+/-)-methyl 2-hydroxy-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylates, and as the major product a 1,3-cycloadduct, methyl (1RS,4RS,5RS)-(2-oxa-3-azabicyclo[3.3.0]oct-7-ene)-4-carboxylate. The similar reaction using cyclopentene (CP) provided only the 1,3-cycloadduct methyl (1SR,4RS,5SR)-(2-oxa-3-azabicyclo[3.3.0]octane)4-carboxylate. The influence of various parameters on the reaction outcome was studied and, based on the results obtained, a mechanism for the formation of both 1,3- and 1,4-cycloadducts is proposed. The structure of all adducts was confirmed by NMR spectroscopic data and/or by X-ray crystallography.

Idioma: Inglês

Tipo (Avaliação Docente): Científica

Nº de páginas: 6