Diels-Alder approach to polysubstituted biaryls

ORGN 99

Bradley O. Ashburn, ashburnb@onid.orst.edu and Rich G. Carter, rich.carter@oregonstate.edu. Department of Chemistry, Oregon State University, 153 Gilbert Hall, Corvallis, OR 97331
 

Biaryl compounds have attracted considerable 
synthetic interest due to their presence in natural products and broad use in transition metal and organocatalysis.  Our laboratory has developed a rapid and atom economical approach to the synthesis of a wide range of highly customizable biaryl templates.  Utilizing the Diels-Alder reaction, tetra-ortho-substituted biaryls can be been synthesized in only 3-4 steps from commercially available materials.  Further functionalization and application as well as the synthesis of axially chiral biaryls will be discussed.