Three-Component Domino Knoevenagel/Vinylogous Michael Reaction: Entry to Challenging o-Terphenyls
Three-Component Domino Knoevenagel/Vinylogous Michael Reaction: Entry to Challenging o-Terphenyls
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DOI：
10.1002/chem.201800048
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发表时间：
2018-05-02
影响因子：
4.3
通讯作者：
Tsogoeva, Svetlana B.
中科院分区：
文献类型：
--
作者：
Grau, Dominik;Grau, Benedikt W.;Tsogoeva, Svetlana B.
报道了一种前所未有的有机催化三组分多米诺Knoevenagel/乙烯基醚Michael反应，该反应由简单的可烯醇化醛、丙二腈和硝基烯烃开始。这种简单的两步多米诺骨牌方法提供了一种直接的立体选择性路线，以多官能乙烯基丙二腈产品（高达82%收率，85：15 d.r.）含有硝基烷烃部分，并有助于可持续性和原子经济性的发展。通过随后的新的三步多米诺反应，包括环化-互变异构化-芳构化步骤，所获得的多米诺产品的高度官能化的邻三联苯（材料科学和药物化学的高度兴趣）的合成的应用已被证明。
An unprecedented organocatalytic three-component domino Knoevenagel/vinylogous Michael reaction starting from simple enolizable aldehydes, malononitrile, and nitroolefins is reported. This facile two-step domino process provides a straightforward stereoselective route to multifunctional vinyl malononitrile products (up to 82% yield, 85:15 d.r.) containing a nitroalkane moiety, and contributes to the development of sustainability and atom economy. The application of the obtained domino products for synthesis of highly functionalized o-terphenyls (of high interest for materials science and medicinal chemistry) through subsequent new three-step domino reaction involving cyclization-tautomerization-aromatization steps, has been demonstrated.