硝甲烷对（2-亚氨基芳基）二乙烯基酮的三重亲核进攻：六氢菲啶酮的多米诺合成策略。
Triple Nucleophilic Attack of Nitromethane on (2-Iminoaryl)divinyl Ketones: A Domino Synthetic Strategy for Hexahydrophenanthridinones.
机构信息
Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University , Changchun 130024, China.
College of Chemistry, Chemical Engineering and Materials Science, Collaborative Innovation Center of Functionalized Probes for Chemical Imaging in Universities of Shandong, Key Laboratory of Molecular and Nano Probes, Ministry of Education, Shandong Normal University , Jinan 250014, China.
出版信息
J Org Chem. 2018 Feb 2;83(3):1232-1240. doi: 10.1021/acs.joc.7b02759. Epub 2018 Jan 16.
A novel domino reaction of (2-iminoaryl)divinyl ketones with nitromethane was developed for the efficient synthesis of hexahydrophenanthridin-9(5H)-ones. The reaction proceeded smoothly from readily available starting materials under mild reaction conditions to construct three new bonds and two rings with high diastereoselectivities in good to excellent yields in a single step. A mechanism is proposed, involving a stepwise double Michael addition/aza-Henry reaction cascade, and in this transformation, nitromethane acts as a trinucleophile.
发展了一种（2-亚氨基芳基）二乙烯基酮与硝基甲烷的新型级联反应，用于高效合成六氢菲并[9,5-h]异喹啉-9(5H)-酮。该反应从易得的起始原料在温和的反应条件下顺利进行，以高非对映选择性和良好至优秀的收率一步构建了三个新键和两个环。提出了一个涉及分步双迈克尔加成/氮杂 Henry 反应级联的机理，在这种转化中，硝基甲烷作为三亲核试剂。
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