Aziridines from aryldiazoacetates with selected imines via ylide intermediates

ORGN 209

Ngozi Onyia, nonyia@umd.edu, Darren Bykowski, dbykowsk@mail.umd.edu, and Michael P. Doyle. Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742
An effective catalytic methodology for aziridination by reactions of methyl aryldiazoacetates with selected N-aryl benzaldimines catalyzed by rhodium acetate is presented. Reactions were performed in refluxing dichloromethane using only a 10% molar excess of imine. Product yields ranged from 53 – 82%. Aziridination is stereospecific, dependent on the stability of the intermediate azomethine ylide, and in all cases only the E isomer is observed.

 

Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Combinatorial, Parallel, and Solid-Phase Chemistry
8:00 PM-10:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 11 September 2006 Moscone Center -- Hall D, Sci-Mix

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006