Synthesis and reactivity of aminoboron compounds

ORGN 146

SA. Westcott, swestcott@mta.ca1, J.M. Blacquiere1, J.D. Webb1, S.M.H. Kabir1, CM. Vogels1, and Andreas Decken2. (1) Department of Chemistry, Mount Allison University, 63C York Street, Sackville, NB E4L 1G8, Canada, (2) Department of Chemistry, University of New Brunswick, Fredericton, E3B 5A3, Canada
Compounds containing boronic acids [RB(OH)2] or boronate esters [RB(OR')2] have been used extensively as synthons in the Suzuki-Miyaura cross-coupling reaction for a variety of applications. Interest in these compounds also arises from their potent biological activities. For instance, aminoboronic acids are among the most potent inhibitors of serine proteases, a diverse group of proteolytic enzymes responsible for the generation of most disease processes. The synthesis of aminoboronic acid-containing compounds, however, is often a complicated procedure requiring several complex organic transformations. We report herein two methodologies for producing these potentially valuable compounds.