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通过芳基亚甲基环丙烷的硅氢化反应催化不对称构建含碳和硅手性中心的硅杂环戊烷

Catalytic Asymmetric Construction of C- and Si-Stereogenic Silacyclopentanes via Hydrosilylation of Arylmethylenecyclopropanes.

作者信息

Wu Liexin, Zhang Lu, Guo Jiandong, Gao Jihui, Ding Yang, Ke Jie, He Chuan

机构信息

Shenzhen Grubbs Institute and Department of Chemistry Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, Guangdong, 518055, China.

Institute for Innovative Materials and Energy School of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu, 225002, China.

出版信息

Angew Chem Int Ed Engl. 2024 Nov 25;63(48):e202413753. doi: 10.1002/anie.202413753. Epub 2024 Oct 17.

Abstract

Silacycles have exhibited significant potential for application in the fields of medicinal chemistry, agrochemistry, and materials science. Accordingly, the development of effective methods for synthesizing these compounds has attracted increasing attention. Here, we report an efficient Cu-catalyzed enantioselective hydrosilylation of arylmethylenecyclopropanes with hydrosilanes, that allows the rapid assembly of various enantioenriched carbon- and silicon-stereogenic silacyclopentanes in good yields with excellent enantioselectivities and diastereoselectivities under mild conditions. Further stereospecific transformation of the Si-H bond on the chiral silicon center expands the diversity of these C- and Si-stereogenic silacyclopentanes.

摘要

硅杂环已在药物化学、农业化学和材料科学领域展现出显著的应用潜力。因此,开发合成这些化合物的有效方法已引起越来越多的关注。在此,我们报道了一种高效的铜催化芳基亚甲基环丙烷与硅烷的对映选择性硅氢化反应,该反应能够在温和条件下以良好的产率、优异的对映选择性和非对映选择性快速组装各种对映体富集的碳和硅立体中心的硅杂环戊烷。手性硅中心上Si-H键的进一步立体专一性转化扩展了这些碳和硅立体中心的硅杂环戊烷的多样性。

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