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

页码：1765 / 1768

页数：4

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