Silylium ions (formally [R 3 Si] + ) have long been the subject of investigations and significant debate in both theoretical and experimental chemistry, but few catalytic, synthetic applications have been reported due to the exceptionally high reactivity and Lewis acidity of these elusive species. Results to be discussed include the application of easily accessible silylium ion catalysts to the stereoselective synthesis of various N-heterocyclic pyrrolidine and piperidine scaffolds. The tested substrates are derived from the chiral pool and can be obtained in three high-yielding steps from amino alcohols; subsequent stereoselective silylium ion catalyzed Prins cyclization and trapping with R 3 Si–Nu nucleophiles (e.g., Nu = H, allyl, azide, and enol ethers) results in novel nitrogen-containing polycyclic scaffolds with potential medicinal chemistry applications.

中文翻译：

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驯服硅离子进行合成：通过立体选择性 C-C 键形成合成 N-杂环

硅离子（原 [R 3 Si] + ）长期以来一直是理论和实验化学研究和重大争论的主题，但由于这些难以捉摸的物种具有极高的反应性和路易斯酸度，因此很少有催化合成应用的报道. 要讨论的结果包括易于获得的甲硅烷离子催化剂在各种 N-杂环吡咯烷和哌啶支架的立体选择性合成中的应用。测试的底物来自手性库，可以从氨基醇中通过三个高产步骤获得；随后的立体选择性甲硅烷离子催化 Prins 环化并用 R 3 Si-Nu 亲核试剂（例如，Nu = H、烯丙基、叠氮化物、