Asymmetric Aminocatalysis in the Synthesis of δ-Lactone Derivatives
Asymmetric Aminocatalysis in the Synthesis of δ-Lactone Derivatives
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DOI：
10.1002/ajoc.201600272
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发表时间：
2016-09-01
影响因子：
2.7
通讯作者：
Albrecht, Lukasz
中科院分区：
文献类型：
--
作者：
Albrecht, Anna;Skrzynska, Anna;Albrecht, Lukasz
在这份手稿中，提出了一种 3,4-二氢香豆素的新方法。它利用 2,4-二醛和香豆素甲酸乙酯之间的氨基催化、三烯胺介导的环加成反应。该反应由带有氢键方酰胺结构单元的双功能氨基催化剂促进。因此，立体化学结果是通过催化剂的氢键部分和亲二烯体之间的双氢键相互作用来控制的。介绍了将获得的环加合物转化为带有双内酯结构基序的 3,4-二氢香豆素。
In this manuscript, a novel approach to 3,4-dihydrocoumarins is presented. It utilizes the aminocatalytic, trienamine-mediated cycloaddition reaction between 2,4-dienals and ethyl coumarincarboxylates. The reaction is promoted by a bifunctional aminocatalyst bearing a hydrogen-bonding squaramide structural unit. As a consequence, the stereochemical outcome is governed through the double hydrogen-bonding interactions between the hydrogen-bonding moiety of the catalyst and the dienophile. The transformation of the obtained cycloadducts into 3,4-dihydrocoumarins bearing a bislactone structural motif is presented.