The objectives of this work are two fold. Professor Holt first proposes to investigate the transition metal catalyzed rearrangement of 2H-azirines into pyrroles and indoles. This initial work will produce vinyl pyrroles which will be used in the synthesis of beta- lactams containing pyrrole ring substituents. Vinyl and aryl-2H-azirines will be prepared initially and a nickel mediated rearrangement of these substrates into vinyl pyrroles and indoles will be effected. The vinyl pyrrole products of this first work will be aziridinated and the aziridine products will be carbonylated to produce the beta-lactams.
With this Minority Research Planning Grant award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. Herman L. Holt, Jr. of the Department of Chemistry at the University of North Carolina at Asheville. Dr. Holt will work on the preparation of a class of chemical compounds known as vinyl pyrroles and indoles and then work on the conversion of these compounds into beta lactams. New methods for the production of beta lactams could have future practical applications since this functional group is found in some antibiotics and antitumor agents. Students trained during the course of this work will gain skills needed by the speciality chemicals and pharmaceutical industries.