A redox-enabled strategy for intramolecular hydroamination

Chem Sci. 2022 May 30;13(24):7264-7268. doi: 10.1039/d2sc00481j. eCollection 2022 Jun 22.

ABSTRACT

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.

PMID:35799811 | PMC:PMC9214914 | DOI:10.1039/d2sc00481j

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