Stereodefined synthesis of cyclic amidines by domino 1,7-H shift and 6π electrocyclisation

Matthew L. Martin; Claire Wilson; Alistair Boyer

doi:10.1039/D3CC01127E

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Stereodefined synthesis of cyclic amidines by domino 1,7-H shift and 6π electrocyclisation†

Matthew L. Martin,^a Claire Wilson

^a and Alistair Boyer

*^a

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* Corresponding authors

^a School of Chemistry, University of Glasgow, UK
E-mail: alistair@boyer-research.com

Abstract

Unsaturated N²-sulfonyl amidines are transformed into valuable N-heterocyclic products when heated with BF₂OTf. Mechanism studies suggest a domino 1,7-H shift, activating a C–H bond, followed by electrocylisation that results in stereodefined cyclic amidines.

This article is part of the themed collections: 2023 Pioneering Investigators and Chemical Communications HOT Articles 2023

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DOI: https://doi.org/10.1039/D3CC01127E
Article type: Communication
Submitted: 06 Mar 2023
Accepted: 29 Mar 2023
First published: 04 Apr 2023
This article is Open Access

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Chem. Commun., 2023,59, 4899-4902

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Stereodefined synthesis of cyclic amidines by domino 1,7-H shift and 6π electrocyclisation

M. L. Martin, C. Wilson and A. Boyer, Chem. Commun., 2023, 59, 4899 DOI: 10.1039/D3CC01127E

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Chemical Communications

Stereodefined synthesis of cyclic amidines by domino 1,7-H shift and 6π electrocyclisation†

Abstract

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Stereodefined synthesis of cyclic amidines by domino 1,7-H shift and 6π electrocyclisation

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