通过涉及硅氧基烯丙基阳离子中间体的级联环加成反应合成功能化的四氢吡喃。
Synthesis of functionalized tetrahydropyrans via cascade cycloaddition involving silyloxyallyl cation intermediates.
机构信息
Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, LA 70803, USA.
出版信息
Chem Commun (Camb). 2020 May 7;56(37):5034-5037. doi: 10.1039/d0cc01796e. Epub 2020 Apr 3.
Abstract
An expedient synthesis of highly substituted tetrahydrobenzofuran via an unsymmetrical silyloxyallyl cation is reported. Conveniently generated under catalytic Brønsted acid conditions, nucleophilic capture of this reactive intermediate by silylenolate, followed by Paal-Knorr cascade cyclization in the presence of tosic acid monohydrate effectively constructed the tetrahydrobenzofuran core in a single synthetic step.
摘要
本文报道了一种通过非对称硅氧基烯丙基阳离子高效合成高取代的四氢苯并呋喃的方法。在催化布朗斯特酸条件下方便地生成，该反应中间体被硅烯醇盐亲核捕获，随后在一水对甲苯磺酸存在下进行 Paal-Knorr 级联环化，有效地在单步合成中构建了四氢苯并呋喃核心。
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Synthesis of functionalized tetrahydropyrans via cascade cycloaddition involving silyloxyallyl cation intermediates.通过涉及硅氧基烯丙基阳离子中间体的级联环加成反应合成功能化的四氢吡喃。
Chem Commun (Camb). 2020 May 7;56(37):5034-5037. doi: 10.1039/d0cc01796e. Epub 2020 Apr 3.
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Correction: Synthesis of functionalized tetrahydropyrans via cascade cycloaddition involving silyloxyallyl cation intermediates.更正：通过涉及甲硅烷氧基烯丙基阳离子中间体的级联环加成反应合成官能化四氢吡喃。
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