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Diastereoselectivity in Diels-Alder Cycloadditions of Erythrose Benzylideneacetal 1,3-Butadienes with Maleimides

Title
Diastereoselectivity in Diels-Alder Cycloadditions of Erythrose Benzylideneacetal 1,3-Butadienes with Maleimides
Type
Article in International Scientific Journal
Year
2012
Authors
Salgueiro, DAL
(Author)
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Duarte, VCM
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Sousa, CEA
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Alves, MJ
(Author)
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Fortes, AG
(Author)
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Journal
Title: SynlettImported from Authenticus Search for Journal Publications
Vol. 23
Pages: 1765-1768
ISSN: 0936-5214
Publisher: Thieme
Other information
Authenticus ID: P-002-8BZ
Abstract (EN): Maleimides were combined with D-erythrose benzylidene-acetal 1,3-butadienes to study the facial selectivity of the Diels-Alder cycloadditions. The selectivity was found to range from moderate to good. The reaction diastereotopicity can be reversed with the temperature. Simultaneous coordination of the diene, having a free hydroxy group, and maleimide to a chiral bimetallic Lewis acid catalyst (LACASA-DA reaction) occurs with complete diastereocontrol to give a single adduct, using an extra chiral inductor either (R)- or (S)-BINOL.
Language: English
Type (Professor's evaluation): Scientific
No. of pages: 4
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