硅叶立德促进的偕胺肟与烯丙基三甲基硅烷的区域和立体选择性碳硅烷化反应。
Silylium-Catalyzed Regio- and Stereoselective Carbosilylation of Ynamides with Allylic Trimethylsilanes.
机构信息
Departamento de Química Orgánica e Inorgánica, Instituto Universitario de Química Organometálica "Enrique Moles", Universidad de Oviedo, Julián Clavería, 8, 33006 Oviedo, Spain.
Departamento de Química, Centro de Investigación en Síntesis Orgánica, Universidad de la Rioja, Madre de Dios, 51, 26006 Logroño, Spain.
出版信息
Org Lett. 2023 Feb 17;25(6):1020-1024. doi: 10.1021/acs.orglett.3c00221. Epub 2023 Feb 7.
The regio- and stereoselective carbosilylation of tosylynamides with allylic trimethylsilanes takes place under mild conditions in the presence of catalytic TMSNTf or HNTf to give ()-α-allyl-β-trimethylsilylenamides with good yields. Theoretical calculations show the activation of the C-C triple bond of the ynamides by the trimethylsilylium ion and formation of a β-trimethylsilylketenimonium cation. Further transformations of the products demonstrate the synthetic utility of this reaction.
在 TMSNTf 或 HNTf 的催化作用下，温和条件下，烯丙基三甲基硅烷与对甲苯磺酰基腙发生区域和立体选择性碳硅烷化反应，以良好的收率得到（）-α-烯丙基-β-三甲基甲硅烷基烯胺。理论计算表明，三甲基硅鎓离子活化了腙的 C-C 三键，并形成了β-三甲基甲硅烷基亚烯酮翁阳离子。产物的进一步转化证明了该反应的合成实用性。
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