Bronsted Acid Catalyzed Addition of Enamides to ortho-Quinone Methide Imines-An Efficient and Highly Enantioselective Synthesis of Chiral Tetrahydroacridines
Bronsted Acid Catalyzed Addition of Enamides to ortho-Quinone Methide Imines-An Efficient and Highly Enantioselective Synthesis of Chiral Tetrahydroacridines
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DOI：
10.1002/anie.201604201
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发表时间：
2016-08-08
影响因子：
16.6
通讯作者：
Schneider, Christoph
中科院分区：
文献类型：
--
作者：
Kretzschmar, Martin;Hodik, Tomas;Schneider, Christoph
通过磷酸催化烯胺与原位生成的邻苯二酮甲酰亚胺的加成反应和随后的消除反应，实现了四氢吖啶类化合物的直接和高对映选择性合成。这一新的一步合成方法是合成具有1，4-二氢喹啉基元的有价值的N-杂环的一种非常有效、优雅和选择性的方法。通过后续的高非对映选择性加氢和N-脱保护反应，反应产物很容易转化为具有三个新的立体中心的游离六氢吖啶。
The direct and highly enantioselective synthesis of tetrahydroacridines was achieved through the phosphoric acid catalyzed addition of enamides to in situ generated orthoquinone methide imines and subsequent elimination. This novel one-step process constitutes a very efficient, elegant, and selective synthetic approach to valuable N-heterocycles with a 1,4-dihydroquinoline motif. By subsequent highly diastereo-selective hydrogenation and N-deprotection the reaction products were easily converted into free hexahydroacridines with a total of three new stereogenic centers.