Asymmetric [3+2]-Cycloaddition of Morita–Baylis–Hillman Carbonates with Maleimides Catalyzed by Chiral Ferrocenylphosphines
Asymmetric [3+2]-Cycloaddition of Morita–Baylis–Hillman Carbonates with Maleimides Catalyzed by Chiral Ferrocenylphosphines
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DOI：
10.1080/00397911.2014.943346
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发表时间：
2014-07
影响因子：
2.1
通讯作者：
Aiping Tu;H. Hu;Tieqi Du;W. Zhong
中科院分区：
文献类型：
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作者：
Aiping Tu;H. Hu;Tieqi Du;W. Zhong
摘要通过简单的合成方法设计并制备了新型手性二茂铁基膦LB 1-LB 9。将这些二茂铁膦用于Morita-Baylis-Hillman碳酸酯与马来酰亚胺的不对称[3+2]-环加成反应，结果表明，LB 7具有良好的催化活性，在温和的反应条件下，以59%的产率和53%ee得到相应的多官能环戊烯.提出了一个合理的反应机理。图形摘要
Abstract New chiral ferrocenylphosphines LB1–LB9 were designed and prepared through simple synthetic approaches. These air-stable ferrocenylphosphines were applied to promote asymmetric [3+2]-cycloaddition of Morita–Baylis–Hillman carbonates with maleimides, among which LB7 was shown to have good catalytic activity to afford the corresponding multifunctional cyclopentenes in up to 59% yield and up to 53% ee under mild reaction conditions. A plausible reaction mechanism was proposed. GRAPHICAL ABSTRACT