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Synfacts 2025; 21(07): 694
DOI: 10.1055/a-2601-4800
Metals in Synthesis

Titanium-Catalyzed Radical Kinetic Resolution of Aziridines Using Water as Hydrogen Atom Donor

Contributor(s):
Martin Oestreich 
,
Hendrik F. T. Klare 
,
Phillip Pommerening 
Yang S, Li L, Wang F, Dong X, Jiang J, Zhang Y-Q *. Shandong University, Jinan, P. R. China
Water-Mediated Radical Kinetic Resolution of Terminal Activated N-Carbamate Aziridines.

J. Am. Chem. Soc. 2025;
147: 13039-13049
DOI: 10.1021/jacs.5c03408
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Keywords

N-carbamate aziridines - radical kinetic resolution - titanium catalysis

Significance

Zhang and co-workers disclosed a protocol for the water-mediated radical kinetic resolution of N-carbamate aziridines using a dinuclear titanium(III) salen complex. This approach allows the resolution of a wide range of terminal aziridines with various carbamate protecting groups and substituents such as alkenyl, alkynyl or aryl groups.


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Comment

The dinuclear titanium(III) catalyst enables both the activation of the racemic aziridines and water as a sustainable hydrogen-atom donor. Experimental investigations, including UV titration to validate the proposed substrate binding behavior, variation of the hydrogen-atom donor and DFT calculations, support the shown mechanism.


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Publication History

Article published online:
23 June 2025

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