Department of Chemistry, The Hong Kong University of Science and Technology , Clear Water Bay, Kowloon, Hong Kong SAR, China.
J Am Chem Soc. 2015 Jan 14;137(1):383-9. doi: 10.1021/ja510980d. Epub 2014 Dec 23.
A new organocatalytic transfer hydrogenation strategy for the asymmetric synthesis of 1,1-diarylethanes is described. Under mild conditions, a range of 1,1-diarylethanes substituted with an o-hydroxyphenyl or indole unit could be obtained with excellent efficiency and enantioselectivity. We also extended the protocol to an unprecedented asymmetric hydroarylation of 1,1-diarylalkenes with indoles for the synthesis of a range of highly enantioenriched 1,1,1-triarylethanes bearing acyclic all-carbon quaternary stereocenters. These diaryl- and triarylethanes exhibit impressive cytotoxicity against a number of human cancer cell lines. Preliminary mechanistic studies combined with DFT calculations provided important insight into the reaction mechanism.
描述了一种用于 1,1-二芳基乙烷不对称合成的新型有机催化转移氢化策略。在温和条件下，一系列带有邻羟基苯基或吲哚单元的 1,1-二芳基乙烷可以以优异的效率和对映选择性得到。我们还将该方案扩展到 1,1-二芳基烯烃与吲哚的前所未有的不对称氢芳基化反应，以合成一系列具有非循环全碳季碳立体中心的高对映富集的 1,1,1-三芳基乙烷。这些二芳基和三芳基乙烷对多种人类癌细胞系表现出令人印象深刻的细胞毒性。初步的机理研究结合密度泛函理论计算为反应机理提供了重要的见解。
