[1,2]-Rearrangement of iminium salts provides access to heterocycles with adamantane scaffold

Benjamin Zonker; Ediz Duman; Heike Hausmann; Jonathan Becker; Radim Hrdina

doi:10.1039/D0OB01156H

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[1,2]-Rearrangement of iminium salts provides access to heterocycles with adamantane scaffold†

Benjamin Zonker,

^a Ediz Duman,^a Heike Hausmann,^a Jonathan Becker^b and Radim Hrdina

*^a

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* Corresponding authors

^a Institute of Organic Chemistry, Justus-Liebig University, Heinrich-Buff-Ring 17, 35392 Giessen, Germany
E-mail: radim.hrdina@org.chemie.uni-giessen.de

^b Institute of Inorganic and Analytical Chemistry, Justus-Liebig University, Heinrich-Buff-Ring 17, 35392 Giessen, Germany

Abstract

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.

This article is part of the themed collection: Synthetic methodology in OBC

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DOI: https://doi.org/10.1039/D0OB01156H
Article type: Communication
Submitted: 03 Jun 2020
Accepted: 22 Jun 2020
First published: 22 Jun 2020

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Org. Biomol. Chem., 2020,18, 4941-4945

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[1,2]-Rearrangement of iminium salts provides access to heterocycles with adamantane scaffold

B. Zonker, E. Duman, H. Hausmann, J. Becker and R. Hrdina, Org. Biomol. Chem., 2020, 18, 4941 DOI: 10.1039/D0OB01156H

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Organic & Biomolecular Chemistry

[1,2]-Rearrangement of iminium salts provides access to heterocycles with adamantane scaffold†

Abstract

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[1,2]-Rearrangement of iminium salts provides access to heterocycles with adamantane scaffold

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