亚胺盐的[1,2]-重排反应为构建具有金刚烷骨架的杂环化合物提供了途径。
[1,2]-Rearrangement of iminium salts provides access to heterocycles with adamantane scaffold.
作者信息
Zonker Benjamin, Duman Ediz, Hausmann Heike, Becker Jonathan, Hrdina Radim
机构信息
Institute of Organic Chemistry, Justus-Liebig University, Heinrich-Buff-Ring 17, 35392 Giessen, Germany.
Institute of Inorganic and Analytical Chemistry, Justus-Liebig University, Heinrich-Buff-Ring 17, 35392 Giessen, Germany.
出版信息
Org Biomol Chem. 2020 Jul 8;18(26):4941-4945. doi: 10.1039/d0ob01156h.
We describe a Brønsted acid-catalysed cascade reaction consisting of a Wagner-Meerwein rearrangement and a subsequent intra- or intermolecular Friedel-Crafts reaction leading to adamantane-based heterocycles. In contrast to the reported W.-M. rearrangements, in this case an iminium moiety serves as the acceptor of a migrating nucleophilic alkyl group in a [1,2]-alkyl shift.
我们描述了一种布朗斯特酸催化的级联反应，该反应由瓦格纳-米尔温重排以及随后的分子内或分子间傅克反应组成，生成基于金刚烷的杂环化合物。与已报道的瓦格纳-米尔温重排不同，在这种情况下，亚胺离子部分在[1,2]-烷基迁移中作为迁移亲核烷基的受体。
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