Formal Dearomative Hydroamination of 2-Arylphenols
An acid-promoted dearomative rearrangement of <i>O</i>-arylhydroxylamines affords 2-aminocyclohexadien-1-ones, which can in turn be reductively quenched for the synthesis of <i>trans</i>-aminoalcohols on a cyclohexadiene core. This method serves as an efficient entry to the pharmaceutically relevant 1-arylcyclohexylamine scaffold in two steps (one purification) from commercially available or readily prepared 2-arylphenols.
Authors
- Robert E. Wiley (ORCID: https://orcid.org/0009-0006-5345-7057)
- Aidan J. Clarkson (ORCID: https://orcid.org/0009-0003-1229-2821)
- Michael Eng (ORCID: https://orcid.org/0000-0003-2144-3057)
- Jeffrey S. Johnson (ORCID: https://orcid.org/0000-0001-8882-9881)
Institutions
- University of North Carolina at Chapel Hill (US)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-12-20
- DOI
- https://doi.org/10.1021/acs.joc.4c02654
- Citations
- 1
- Primary Topic
- Asymmetric Synthesis and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 0.25
Funders
- National Science Foundation
- National Institute of General Medical Sciences
- Division of Chemistry