Enabling Unfavorable Hydroamination Reactions Using a Chemoselective N-O Bond Reduction.

Autor:	Ly HM; Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie-Curie, Ottawa, Ontario K1N 6N5, Canada., Almeneim H; Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie-Curie, Ottawa, Ontario K1N 6N5, Canada., Gill MA; Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie-Curie, Ottawa, Ontario K1N 6N5, Canada., Keillor JW; Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie-Curie, Ottawa, Ontario K1N 6N5, Canada., Beauchemin AM; Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie-Curie, Ottawa, Ontario K1N 6N5, Canada.
Jazyk:	angličtina
Zdroj:	Organic letters [Org Lett] 2024 Nov 07. Date of Electronic Publication: 2024 Nov 07.
DOI:	10.1021/acs.orglett.4c03688
Abstrakt:	Despite major advances, intramolecular alkene hydroamination reactions often face limitations. Herein, a redox-enabled process featuring oxidation of an amine to a hydroxylamine, a concerted hydroamination step, followed by catalytic reduction of N -oxide is shown to be broadly applicable. Catalyst screening and optimization showed that a K 2 OsO 2 (OH) 4 -pinacol complex rapidly and chemoselectively reduces the N -oxide cycloadduct in the presence of hydroxylamine and dimethyl sulfoxide. This selectivity was exploited to drive the equilibria toward complex products.
Databáze:	MEDLINE
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