Highly diastereoselective synthesis of 2-azabicyclo[2.2.1]hept-5-ene derivative...

• Autor(es): García-Mera, Xerardo ; Rodríguez-Borges, José E. ; Vale, M. Luísa C. ; Alves, M. José
• Data: 2011
• Identificador Persistente: http://hdl.handle.net/1822/15667
• Origem: RepositóriUM - Universidade do Minho
• Assunto(s): Asymetric synthesis; Cycloadditions; Aza-Diels-Alder reaction; Induction; Chiral auxiliaries
• Tipo de Documento: Artigo
• Idioma: Inglês

Descrição

The cycloaddition between protonated glyoxylate imines possessing two chiral auxiliaries, N-(S)- or N-(R)-1-phenylethyl and (-)-8-phenylmenthyl or (+)-8- phenylneomenthyl, and cyclopentadiene is described. The absolute configuration of all adducts formed was unequivocally assigned through NMR, specific optical rotation and X-ray data of appropriated derivatives. Experimental results confirm the highly exoselectivity for these aza-Diels–Alder reactions, single adducts being obtained from combinations of (8PM)-(R-PEA) and (8PNM)-(S-PEA).