Formal Dearomative Hydroamination of 2-Arylphenols

An acid-promoted dearomative rearrangement of -arylhydroxylamines affords 2-aminocyclohexadien-1-ones, which can in turn be reductively quenched for the synthesis of -aminoalcohols on a cyclohexadiene core. This method serves as an efficient entry to the pharmaceutically relevant 1-arylcyclohexylami...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-12
Main Authors: Wiley, Robert E, Eng, Michael C, Clarkson, Aidan J, Johnson, Jeffrey S
Format: Article
Language:English
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Summary:An acid-promoted dearomative rearrangement of -arylhydroxylamines affords 2-aminocyclohexadien-1-ones, which can in turn be reductively quenched for the synthesis of -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.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c02654