Phosphine-Catalyzed Asymmetric Intermolecular Cross-Vinylogous Rauhut-Currier Reactions of Vinyl Ketones with para-Quinone Methides
Phosphine-Catalyzed Asymmetric Intermolecular Cross-Vinylogous Rauhut-Currier Reactions of Vinyl Ketones with para-Quinone Methides
复制标题
膦催化乙烯基酮与对醌甲基化物的不对称分子间交叉乙烯基 Rauhut-Currier 反应
DOI：
10.1021/acscatal.7b00030
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发表时间：
2017-04-01
期刊：
影响因子：
12.9
通讯作者：
Zhang, Junliang
中科院分区：
文献类型：
--
作者：
Li, Shenhuan;Liu, Yuanyuan;Zhang, Junliang
开发了一种手性酰胺-膦双功能催化剂，并成功应用于烷基乙烯基酮与对醌甲基化物的不对称分子间交叉乙烯基Rauhut-Currier反应，具有优异的区域选择性和立体选择性（高达>99%对映体过量（ee））。该方法提供了一种容易获得结构多样、广泛存在的二芳基次甲基立体中心的方法，具有优异的对映选择性。已经进行了密度泛函理论（DFT）计算，以了解这种膦催化不对称转化的机制和对映选择性。
A chiral amide-phosphine bifunctional catalyst was developed and successfully applied to the asymmetric intermolecular cross-vinylogous Rauhut-Currier of alkyl vinyl ketones with para-quinone methides, offering excellent regioselectivity and stereoselectivity (up to >99% enantiomeric excess (ee)). This method provides a facile access to structurally diverse widely existed diarylmethine stereogenic centers with excellent enantioselectivity. Density functional theory (DFT) calculations have been performed to understand the mechanism and enantioselectivity for this phosphinecatalyzed asymmetric transformation.