Asymmetric Catalytic [4+5] Annulation of ortho-Quinone Methides with Vinylethylene Carbonates and its Extension to Stereoselective Tandem Rearrangement
Asymmetric Catalytic [4+5] Annulation of ortho-Quinone Methides with Vinylethylene Carbonates and its Extension to Stereoselective Tandem Rearrangement
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不对称催化[4 5]邻醌甲基化物与乙烯基碳酸乙烯酯的环化及其对立体选择性串联重排的扩展
DOI：
10.1002/chem.201904903
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发表时间：
2020-03-03
影响因子：
4.3
通讯作者：
Fan, Chun-An
中科院分区：
文献类型：
--
作者：
An, Xian-Tao;Du, Ji-Yuan;Fan, Chun-An
首次报道了钯催化邻醌甲基化物（o-QMs）与取代乙烯基碳酸亚乙酯（VEC）的不对称[4+5]成环反应，为手性九元苯并杂环化合物的合成提供了一种新的对映选择性方法.在此基础上，首次在室温下进行了硅胶促进的不对称芳香Claisen重排反应，为不对称构筑手性功能化高烯丙醇类化合物的季碳中心提供了一种新的方法.
Palladium-catalyzed asymmetric [4+5] annulation of ortho-quinone methides (o-QMs) with substituted vinylethylene carbonates (VECs) is described for the first time, giving a novel enantioselective approach to chiral nine-membered benzoheterocycles. Based on this designed [4+5] annulation, an unprecedented silica gel-promoted tandem rearrangement reaction featuring a unique asymmetric aromatic Claisen rearrangement is explored at room temperature, offering a new method for asymmetric construction of all-carbon quaternary stereocenters embedded in chiral functionalized homoallylic alcohols.