Asymmetric cobalt-catalyzed aziridination with azides as nitrene source

ORGN 664

Joshua V. Ruppel, Velusamy Subbarayan, Jess E. Jones, and X. Peter Zhang, Department of Chemistry, University of South Florida, 4202 E Fowler Ave, Tampa, FL 33620
Metal catalyzed nitrene transfer reactions are an attractive route to produce biologically and synthetically important molecules such as amines and aziridines. Although much progress has been made in nitrene transfer reactions utilizing PhI=NTs and related compounds, the nitrene source suffers from several drawbacks. Consequently, there has been growing interest in developing catalytic nitrene transfer reactions using alternate nitrene sources. Previously, we have reported the use of alternate nitrene sources bromamine-T, diphenylphosphoryl azide, and arylsulfonyl azides for catalytic aziridination catalyzed by metalloporphyrins. In our continuing studies to develop metalloporphyrin-catalyzed nitrene transfer reactions, we wish to present the use of a new class of D2-symmetric chiral porphyrin ligands for asymmetric aziridination of olefins with azides as nitrene source. The cobalt-catalyzed process can proceed under mild and neutral conditions without the need of other reagents, while generating nitrogen gas as the only byproduct. These processes produce synthetically and biologically valuable nitrogen containing compounds.

Heterocycles and Aromatics, Asymmetric Reactions and Syntheses and Total Synthesis of Complex Molecules
7:00 PM-9:00 PM, Wednesday, August 19, 2009 Walter E. Washington Convention Center -- Ballroom C, Poster

8:00 PM-10:00 PM, Monday, August 17, 2009 Walter E. Washington Convention Center -- Hall D, Sci-Mix

Division of Organic Chemistry

The 238th ACS National Meeting, Washington, DC, August 16-20, 2009