Organocatalytic Enantioselective Cross-Vinylogous Rauhut-Currier Reaction of Methyl Coumalate with Enals.
Organocatalytic Enantioselective Cross-Vinylogous Rauhut-Currier Reaction of Methyl Coumalate with Enals.
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DOI：
10.1002/anie.201805019
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发表时间：
2018-06
影响因子：
--
通讯作者：
Qiwen Liu;L. Zu
中科院分区：
文献类型：
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作者：
Qiwen Liu;L. Zu
报道了香豆酸甲酯与α，β-不饱和醛的有机催化交叉分子间对映选择性Rauhut-Currier(RC)反应，烯烃被亚胺催化活化为Michael受体，香豆酸甲酯作为活化的二烯生成潜在的烯醇。这种优良的选择性是由香豆酸甲酯的芳香性驱动的，这种杂环结构向其他缺电子芳烃和杂环的转化在一定程度上解决了分子间交叉RC反应具有挑战性的选择性问题和亚胺催化的有限范围。
The organocatalytic enantioselective intermolecular cross-vinylogous Rauhut-Currier (RC) reaction of methyl coumalate with α,β-unsaturated aldehydes is reported, and the enals are activated by iminium catalysis to serve as the Michael acceptors and methyl coumalate is used as an activated diene to generate a latent enolate. The excellent selectivity is driven by the aromaticity of methyl coumalate, and the post transformation of this heterocyclic structure into other electron-deficient arenes and heterocycles have addressed, in part, the challenging selectivity issues of the intermolecular cross-RC reactions and the limited scope of iminium catalysis.