[1,2]-Rearrangement of iminium salts provides access to heterocycles with adamantane scaffold.,Organic & Biomolecular Chemistry

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[1,2]-Rearrangement of iminium salts provides access to heterocycles with adamantane scaffold.
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2020-06-22 , DOI: 10.1039/d0ob01156h
Benjamin Zonker ₁ , Ediz Duman ₁ , Heike Hausmann ₁ , Jonathan Becker ₂ , Radim Hrdina ₁

Affiliation

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.

中文翻译：

[1,2]-亚胺盐的重排提供了进入金刚烷骨架的杂环的途径。

我们描述了由Wagner-Meerwein重排和随后的分子内或分子间Friedel-Crafts反应组成的布朗斯台德酸催化的级联反应，该反应导致金刚烷基杂环。与报告的W.–M相反。重排，在这种情况下，亚胺基部分充当[1,2]-烷基移位中迁移的亲核烷基的受体。

更新日期：2020-07-08

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