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Simultaneous construction of axial and planar chirality by gold/TY-Phos-catalyzed asymmetric hydroarylation
Nature Communications ( IF 16.6 ) Pub Date : 2021-07-29 , DOI: 10.1038/s41467-021-24678-5
Pei-Chao Zhang 1 , Yin-Lin Li 1 , Jiafeng He 1 , Hai-Hong Wu 1 , Zhiming Li 2 , Junliang Zhang 2, 3
Affiliation  

The simultaneous construction of two different chiralities via a simple operation poses considerable challenge. Herein a cationic gold-catalyzed asymmetric hydroarylation of ortho-alkynylaryl ferrocenes derivatives is developed, which enable the simultaneous construction of axial and planar chirality. The here identified TY-Phos derived gold complex is responsible for the high yield, good diastereoselectivity (>20:1 dr), high enantioselectivities (up to 99% ee) and mild conditions. The catalyst system also shows potential application in the synthesis of chiral biaryl compounds. The cause of high enantioselectivity of this hydroarylation is investigated with density functional theory caculation.



中文翻译:

通过金/TY-Phos催化的不对称氢芳基化同时构建轴向和平面手性

通过简单的操作同时构建两种不同的手性提出了相当大的挑战。本文开发了一种阳离子金催化的邻炔基芳基二茂铁衍生物的不对称氢化芳基化,它能够同时构建轴向和平面手性。此处确定的 TY-Phos 衍生的金络合物具有高产率、良好的非对映选择性(>20:1 dr)、高对映选择性(高达 99% ee)和温和的条件。该催化剂体系还显示出在手性联芳基化合物合成中的潜在应用。用密度泛函理论计算研究了这种加氢芳基化的高对映选择性的原因。

更新日期:2021-07-29
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