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Zonker B, Duman E, Hausmann H, et al. [1,2]-Rearrangement of iminium salts provides access to heterocycles with adamantane scaffold. Org Biomol Chem. 2020;18(26):4941-4945doi: 10.1039/d0ob01156h.
Zonker, B., Duman, E., Hausmann, H., Becker, J., & Hrdina, R. (2020). [1,2]-Rearrangement of iminium salts provides access to heterocycles with adamantane scaffold. Organic & biomolecular chemistry, 18(26), 4941-4945. https://doi.org/10.1039/d0ob01156h
Zonker, Benjamin, et al. "[1,2]-Rearrangement of iminium salts provides access to heterocycles with adamantane scaffold." Organic & biomolecular chemistry vol. 18,26 (2020): 4941-4945. doi: https://doi.org/10.1039/d0ob01156h
Zonker B, Duman E, Hausmann H, Becker J, Hrdina R. [1,2]-Rearrangement of iminium salts provides access to heterocycles with adamantane scaffold. Org Biomol Chem. 2020 Jul 08;18(26):4941-4945. doi: 10.1039/d0ob01156h. PMID: 32583843.
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Org Biomol Chem. 2020 Jul 08;18(26):4941-4945. doi: 10.1039/d0ob01156h.

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

Organic & biomolecular chemistry

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

Affiliations

  1. Institute of Organic Chemistry, Justus-Liebig University, Heinrich-Buff-Ring 17, 35392 Giessen, Germany. [email protected].
  2. Institute of Inorganic and Analytical Chemistry, Justus-Liebig University, Heinrich-Buff-Ring 17, 35392 Giessen, Germany.

PMID: 32583843 DOI: 10.1039/d0ob01156h

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.

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