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

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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.

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

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Article information


Submitted
18 Dec 2019
Accepted
24 Jan 2020
First published
04 Feb 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

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

C. Tan, Y. Liu, X. Liu, H. Jia, K. Xu, S. Huang, J. Wang and J. Tan, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/C9QO01489F

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