Synthesis of spirocyclic 1,2-diamines by dearomatising intramolecular diamination of phenols

Anthony Aimon; Mark J. Dow; Abigail R. Hanby; Ephraim A. Okolo; Christopher M. Pask; Adam Nelson; Stephen P. Marsden

doi:10.1039/D2CC06137F

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Synthesis of spirocyclic 1,2-diamines by dearomatising intramolecular diamination of phenols†

Anthony Aimon,

^a Mark J. Dow,

^a Abigail R. Hanby,^a Ephraim A. Okolo,^a Christopher M. Pask,^a Adam Nelson

*^ab and Stephen P. Marsden

*^a

Author affiliations

* Corresponding authors

^a School of Chemistry, University of Leeds, Leeds, UK
E-mail: s.p.marsden@leeds.ac.uk, a.s.nelson@leeds.ac.uk

^b Astbury Centre for Structural Molecular Biology, University of Leeds, Leeds, UK

Abstract

The stereocontrolled synthesis of complex spirotricyclic systems containing an embedded syn-1,2-diaminocyclohexane unit is reported, based upon a dearomatising oxidation of phenols bearing pendant ureas capable of acting as double nucleophiles. This complexity-generating transformation yields products with rich functionality suitable for application in the synthesis of potentially bioactive compounds.

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DOI: https://doi.org/10.1039/D2CC06137F
Article type: Communication
Submitted: 15 Nov 2022
Accepted: 12 Dec 2022
First published: 12 Dec 2022
This article is Open Access

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Chem. Commun., 2023,59, 607-610

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Synthesis of spirocyclic 1,2-diamines by dearomatising intramolecular diamination of phenols

A. Aimon, M. J. Dow, A. R. Hanby, E. A. Okolo, C. M. Pask, A. Nelson and S. P. Marsden, Chem. Commun., 2023, 59, 607 DOI: 10.1039/D2CC06137F

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Chemical Communications

Synthesis of spirocyclic 1,2-diamines by dearomatising intramolecular diamination of phenols†

Abstract

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Synthesis of spirocyclic 1,2-diamines by dearomatising intramolecular diamination of phenols

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