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Issue 17, 2013
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The Ti-BINOLate-catalyzed, enantioselective ring-opening of meso-aziridines with amines

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Abstract

The titanium-BINOLate-catalyzed, highly enantioselective ring-opening reaction of meso-aziridines has been developed which furnishes trans-1,2-diamines in typically good yields and excellent enantioselectivities. N-Aryl aziridines attached to a 5- or 6-membered carbocyclic ring are among the best substrates for this process providing the products in up to >99% ee. The chiral catalyst is easily prepared in situ from commercially available components and does not require any laborious ligand synthesis. Structural investigations into the catalyst composition reveal an oligomeric structure of the active Ti-complex.

Graphical abstract: The Ti-BINOLate-catalyzed, enantioselective ring-opening of meso-aziridines with amines

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Publication details

The article was received on 31 Jan 2013, accepted on 01 Mar 2013 and first published on 21 Mar 2013


Article type: Paper
DOI: 10.1039/C3OB40222C
Citation: Org. Biomol. Chem., 2013,11, 2787-2803
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    The Ti-BINOLate-catalyzed, enantioselective ring-opening of meso-aziridines with amines

    S. Peruncheralathan, S. Aurich, H. Teller and C. Schneider, Org. Biomol. Chem., 2013, 11, 2787
    DOI: 10.1039/C3OB40222C

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