Gold-Catalyzed Hydroamination of Propargylic Alcohols: Controlling Divergent Catalytic Reaction Pathways To Access 1,3-Amino Alcohols, 3-Hydroxyketones, or 3-Aminoketones
Victor Laserna, Michael J. Porter, Tom D. Sheppard*
*Department of Chemistry, Christopher Ingold Laboratories,
University College London, 20 Gordon Street, London WC1H 0AJ, U.K., Email: tom.sheppard
ucl.ac.uk
V. Laserna, M. J. Porter, T. D. Sheppard, J. Org. Chem., 2019, 84, 11391-11406.
DOI: 10.1021/acs.joc.9b00988
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Abstract
A gold-catalyzed hydroamination of propargylic alcohols with anilines provides 3-hydroxyimines. A subsequent reduction gives 1,3-amino alcohols with high syn selectivity. By using a catalytic amount of aniline, 3-hydroxyketones can be obtained in high yield directly from propargylic alcohols. And a selective formation of 3-aminoketones via a rearrangement/hydroamination pathway is also described.
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Key Words
hydration, β-hydroxy ketones, β-amino ketones
ID: J42-Y2019
