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

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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.

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

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Article information


Submitted
03 Jun 2020
Accepted
22 Jun 2020
First published
22 Jun 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Communication

[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, Advance Article , DOI: 10.1039/D0OB01156H

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