Author(s):
Salgueiro, D. A. L. 
; Duarte, Vera C. M. ; Sousa, Cristina ; Alves, M. José ; Fortes, A. Gil
Date: 2012
Persistent ID: http://hdl.handle.net/1822/22057
Origin: RepositóriUM - Universidade do Minho
Document details
Diastereo-selectivity in diels–alder cycloadditions of erythrose benzylidene-ac...
Description
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.
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.
Document Type
Article
Language English
Language English
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