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TitleDiastereo-selectivity in diels–alder cycloadditions of erythrose benzylidene-acetal 1,3-Butadienes with maleimides
Author(s)Salgueiro, D. A. L.
Duarte, Vera C. M.
Sousa, Cristina
Alves, M. José
Fortes, A. Gil
D-erythrose benzylidene-acetal 1,3-butadiene
Diels-Alder cycloaddition
Issue date2012
PublisherGeorg Thieme Verlag
Abstract(s)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.
AccessOpen access
Appears in Collections:CDQuim - Artigos (Papers)

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