Regio- and enantioselective rhodium-catalyzed [2+2+2] carbocyclization reactions

ORGN 253

James R. Sawyer, jrsawyer@indiana.edu and P. Andrew Evans. Department of Chemistry, Indiana University, 800 East Kirkwood Ave, Bloomington, IN 47405
Transition metal-catalyzed [m+n+o] carbocyclization reactions provide powerful methods for the efficient construction of complex polycyclic systems that are generally not accessible through classical pericyclic reactions. Significant attention has been focused on rhodium-catalyzed carbocyclizations due to their unique selectivity and synthetic versatility. We have developed highly regio- and enantioselective rhodium-catalyzed intermolecular [2+2+2] cyclizations between tethered enynes and alkynes for the synthesis of cyclohexadiene ring systems. The scope and limitations of these transformations, as well as their application to target directed synthesis, will be presented.