Issue 17, 2013

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

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

Supplementary files

Article information

Article type
Paper
Submitted
31 Jan 2013
Accepted
01 Mar 2013
First published
21 Mar 2013

Org. Biomol. Chem., 2013,11, 2787-2803

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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