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

被引：4
|
作者：
Salgueiro, Daniela A. L. [1 ]
Duarte, Vera C. M. [1 ]
Sousa, Cristina E. A. [1 ]
Alves, Maria J. [1 ]
Fortes, Antonio Gil [1 ]
机构：
[1] Univ Minho, Dept Quim, P-4710057 Braga, Portugal
来源：
SYNLETT | 2012年 / 12期
关键词：
maleimides; D-erythrose benzylidene-acetal 1,3-butadiene; Diels-Alder cycloaddition; selectivity; PLANE-NONSYMMETRIC CYCLOPENTADIENES; LEWIS-ACID TEMPLATE; FACIAL SELECTIVITY; CHIRAL DIENES; COMPONENTS;
D O I：
10.1055/s-0031-1289785
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
引用
收藏
页码：1765 / 1768
页数：4
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