A redox-enabled strategy for intramolecular hydroamination.
| Autor: | Allen MA; Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa 10 Marie-Curie Ottawa ON K1N 6N5 Canada andre.beauchemin@uottawa.ca., Ly HM; Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa 10 Marie-Curie Ottawa ON K1N 6N5 Canada andre.beauchemin@uottawa.ca., O'Keefe GF; Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa 10 Marie-Curie Ottawa ON K1N 6N5 Canada andre.beauchemin@uottawa.ca., Beauchemin AM; Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa 10 Marie-Curie Ottawa ON K1N 6N5 Canada andre.beauchemin@uottawa.ca. |
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| Jazyk: | angličtina |
| Zdroj: | Chemical science [Chem Sci] 2022 May 30; Vol. 13 (24), pp. 7264-7268. Date of Electronic Publication: 2022 May 30 (Print Publication: 2022). |
| DOI: | 10.1039/d2sc00481j |
| Abstrakt: | Metal- or acid-catalyzed intramolecular hydroamination and Cope-type intramolecular hydroamination, a distinct concerted approach using hydroxylamines, typically suffer from significant synthetic limitations. Herein we report a process for intramolecular hydroamination that uses a redox-enabled strategy relying on efficient in situ generation of hydroxylamines by oxidation, followed by Cope-type hydroamination, then reduction of the resulting pyrrolidine N -oxide. The steps are performed sequentially in a single pot, no catalyst is required, the conditions are mild, the process is highly functional group tolerant, and no chromatography is generally required for isolation. A robustness screen and a gram-scale example further support the practicality of this approach. Competing Interests: There are no conflicts to declare. (This journal is © The Royal Society of Chemistry.) |
| Databáze: | MEDLINE |
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