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Stereoselective synthesis of trans-aziridines via intramolecular oxidative C(sp3)–H amination of β-amino ketones

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Aziridines are ubiquitous in bioactive molecules and often serve as key synthetic building blocks. We report herein an intramolecular KI/TBHP mediated oxidative dehydrogenative C(sp3)–H amination reaction to synthesize a diverse… Click to show full abstract

Aziridines are ubiquitous in bioactive molecules and often serve as key synthetic building blocks. We report herein an intramolecular KI/TBHP mediated oxidative dehydrogenative C(sp3)–H amination reaction to synthesize a diverse array of trans-2,3-disubstituted aziridines in good yields under mild conditions. The synthetic utility of this protocol was further highlighted by a one-pot, two-step synthesis of unprotected aziridines.

Keywords: synthesis trans; stereoselective synthesis; sp3; sp3 amination

Journal Title: Organic chemistry frontiers
Year Published: 2020

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