Enantioselective synthesis of [(1R,3-exo)-2-benzyl-2-azabicyclo[2.2.1]hept-5en-3-yl] methanol via Aza-Diels-Alder reaction

• Tipo: Artigo em Revista Científica Internacional
• Data: 2005

Autores

Fernandez, F (Autor) Outra; Garcia Mera, X (Autor) Outra; Vale, MLC (Autor) FCUP; Rodriguez Borges, JE (Autor) FCUP

Revista

Título: Synlett

Páginas: 319-321

ISSN: 0936-5214

Editora: Thieme

Indexação

ISI Web of Knowledge - 16 Citações

Scopus - 20 Citações

Classificação Científica

FOS: Ciências exactas e naturais > Química

Outras Informações

ID Authenticus: P-000-4ZB

DOI: 10.1055/s-2004-836068

Abstract (EN): The asymmetric aza-Diels-Alder reaction of the 8-phenylneomenthyl (or 8-phenylisomenthyl) glyoxylate-derived N-benzylimine with cyclopentadiene resulted in the enantioselective synthesis of the corresponding [(1R,3-evo)-2-benzyl-2-azabicyclo[2.2.1]hept-5-en-3-yl]carboxylate. In both cases, the (1R,3-exo)-adduct was the main diastereomer and was isolated in 70% and 65% yield, respectively. Reduction of the (1R,3-exo)-adducts with LiAlH4 afforded [(1R,3-exo)-2-benzyl-2-azabicyclo[2.2.1]hept-5-en-3-yl] methanol, with recovery of the chiral auxiliaries with retention of configuration.

Idioma: Inglês

Tipo (Avaliação Docente): Científica

Nº de páginas: 3