Asymmetric Synthesis of Dihydrocoumarins through Chiral Phosphoric Acid-Catalyzed Cycloannulation of para-Quinone Methides and Azlactones.
Asymmetric Synthesis of Dihydrocoumarins through Chiral Phosphoric Acid-Catalyzed Cycloannulation of para-Quinone Methides and Azlactones.
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DOI：
10.1021/acs.joc.7b02750
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发表时间：
2018-01
期刊：
影响因子：
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通讯作者：
Zhi-Pei Zhang;Kai Xie;Chen Yang;Man Li;Xin Li
中科院分区：
文献类型：
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作者：
Zhi-Pei Zhang;Kai Xie;Chen Yang;Man Li;Xin Li
建立了一种手性磷酸催化的二氢香豆素模体的合成方法，即通过偶氮内酯与对苯二酚甲醚(p-QMS)的加成反应。反应进行顺利，反应范围广，以高产率得到相应的产物，具有良好的非对映选择性(>；19：1dr)和对映体选择性(高达99%ee)。提出了两种可能的途径来解释立体选择性。
A chiral phosphoric acid-catalyzed approach constructing dihydrocoumarin motifs by the addition of azlactones to para-quinone methides (p-QMs) was developed. The reaction proceeded smoothly with a wide range of p-QMs and azlactones to generate corresponding products in high yields with excellent diastereoselectivities (>19:1 dr) and enantioselectivities (up to 99% ee). Two possible pathways were proposed to explain the stereoselectivity.