Diastereo-selectivity in diels–alder cycloadditions of erythrose benzylidene-acetal 1,3-Butadienes with maleimides
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...
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| Other Authors: | , , , |
| Format: | article |
| Language: | eng |
| Published: |
2012
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| Subjects: | |
| Online Access: | http://hdl.handle.net/1822/22057 |
| Country: | Portugal |
| Oai: | oai:repositorium.sdum.uminho.pt:1822/22057 |
| Summary: | 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. |
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