Diastereo-selectivity in diels–alder cycloadditions of erythrose benzylidene-ac...

• Autor(es): Salgueiro, D. A. L. ; Duarte, Vera C. M. ; Sousa, Cristina ; Alves, M. José ; Fortes, A. Gil
• Data: 2012
• Identificador Persistente: http://hdl.handle.net/1822/22057
• Origem: RepositóriUM - Universidade do Minho
• Tipo de Documento: Artigo
• Idioma: Inglês

Descrição

Maleimides were combined with D-erythrose benzylidene-acetal 1,3-butadienes 1 and 2 to study the facial selectivity of the Diels-Alder cycloadditions. The selectivity was found to be from moderate to good. The reaction diastereotopicity can be reversed with the temperature. Simultaneous coordination of diene 1, having a free hydroxyl group, and maleimide 3 to a chiral bimetallic Lewis acid catalyst (LACASA-DA reaction) occurs with complete diastereo-control to give a single adduct, using an extra chiral inductor either R- or S-BINOL.