Synfacts 2006(5): 0486-0486  
DOI: 10.1055/s-2006-934423
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Dimerization of Lithiated Terminal Aziridines

Contributor(s): Paul Knochel, Andrei Gavryushin
S. M. Miles, D. M. Hodgson*
University of Oxford, UK
Further Information

Publication History

Publication Date:
21 April 2006 (online)

Significance

The authors developed a simple and useful protocol for the preparation of chiral functionalized 1,4-diamines starting from readily available chiral aziridines. The 1,4-diamine framework is a widespread feature of many natural and synthetic biologically active compounds, such as for instance, pharmacologically important enzyme inhibitors. The reaction is highly stereoselective (only the E-isomer is formed) providing the products in high yield.