Organocatalytic enantioselective construction of Si-stereocenters: recent advances and perspectives,Chemical Society Reviews

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Organocatalytic enantioselective construction of Si-stereocenters: recent advances and perspectives
Chemical Society Reviews ( IF 40.4 ) Pub Date : 2024-08-02 , DOI: 10.1039/d4cs00417e
Zhong-Tian Ye ₁ , Zhong-Wei Wu ₁ , Xue-Xin Zhang ₁ , Jian Zhou ₁ , Jin-Sheng Yu _{1,

2}

Affiliation

Silicon-stereogenic chiral organosilanes have found increasing applications in synthetic chemistry, medicinal chemistry, and materials science. In this context, various asymmetric catalytic methods have been established for the diverse synthesis of silicon-stereogenic silanes. In particular, asymmetric organocatalysis is emerging as an important and complementary synthetic tool for the enantioselective construction of silicon-stereocenters, along with the rapid development of chiral-metal catalyzed protocols. Its advent provides a powerful platform to achieve functionalized silicon-stereogenic organosilanes with structural diversity, and should lead to great development in chiral organosilicon chemistry. In this Tutorial Review, we highlight these latest achievements from two aspects: desymmetrizations of prochiral tetraorganosilanes and dynamic kinetic asymmetric transformations of racemic organosilanes by employing five organocatalytic activation modes. The advantages, limitations and synthetic value of each protocol, as well as the synthetic opportunities still open for further exploration, are also discussed.

中文翻译：

硅立体中心的有机催化对映选择性构建：最新进展和前景

硅立体手性有机硅烷在合成化学、药物化学和材料科学中的应用越来越多。在这方面，已经建立了各种不对称催化方法来合成硅立体硅烷。特别是，随着手性金属催化方案的快速发展，不对称有机催化正在成为硅立体中心对映选择性构建的重要且补充的合成工具。它的出现为实现具有结构多样性的功能化硅立体有机硅烷提供了强大的平台，并将导致手性有机硅化学的巨大发展。在本教程综述中，我们从两个方面重点介绍这些最新成果：前手性四有机硅烷的去对称化和采用五种有机催化活化模式的外消旋有机硅烷的动态动力学不对称转化。还讨论了每个协议的优点、局限性和综合价值，以及仍有待进一步探索的综合机会。

更新日期：2024-08-04

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