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首页> 外文期刊>Chemical science >Enantioselective gold-catalyzed intermolecular [2+2] versus [4+2]-cycloadditions of 3-styrylindoles with N-allenamides: observation of interesting substituent effects
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Enantioselective gold-catalyzed intermolecular [2+2] versus [4+2]-cycloadditions of 3-styrylindoles with N-allenamides: observation of interesting substituent effects

机译:对映选择性金催化的3-苯乙烯基吲哚与 N -亚酰胺基的分子间[2 + 2]对[em> [4 + 2]-环加成反应:观察到有趣的取代基作用

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A highly enantioselective [2+2] versus a [4+2]-cycloaddition of 3-styrylindoles to N-allenamides catalyzed by identical gold(I)/chiral phosphoramidite complexes is presented, which provides facile access to synthetically valuable, optically active substituted cyclobutanes and tetrahydrocarbazoles. The cycloaddition mode unexpectedly depends on the electronic nature of the N-substituent 3-styrylindoles, the origin of which could be well rationalized using DFT calculations and experimental results. To the best of our knowledge, the present work represents the first example of such an impressive substituent effect in tuning the reaction mode with high chemo-, regio- and enantioselectivity in asymmetric gold catalysis.
机译:相同金( I )催化的3-苯乙烯基吲哚对[em> N -亚酰胺的高对映选择性[2 + 2]对[em> 对[4 + 2]-环加成。提出了一种小/)/手性亚磷酰胺络合物,可轻松获得具有合成价值的光学活性取代的环丁烷和四氢咔唑。环加成模式出乎意料地取决于 N 取代基3-styrylindoles的电子性质,使用DFT计算和实验结果可以很好地理清其起源。据我们所知,本工作代表了这种令人印象深刻的取代基效应在不对称金催化中以高化学,区域和对映体选择性调节反应模式的第一个例子。

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