Highly diastereoselective intermolecular [4+2+2] carbocyclization utilizing rhodium(I) N-heterocyclic carbene (NHC) catalyst

ORGN 176

P. Andrew Evans, Aleem N. Fazal, and Erich W Baum. Department of Chemistry, Indiana University, 800 E. Kirkwood, Bloomington, IN 47405

Transition-metal catalyzed cycloadditions provide a powerful tool for construction of fused polycyclic systems. We have developed Rh-catalyzed [4+2+2] intermolecular cyclization of 1,6-enynes with butadiene to afford 5,8-fused polycyclic systems. The diastereoselective nature of the reaction was explored by using Rh-NHC (NHC=N-Heterocyclic Carbene) complexes. The scope and limitation of this reaction will be discussed.

Heterocycles and Aromatics 8:00 AM-12:00 PM, Monday, March 29, 2004 Anaheim Convention Center -- 303D, Oral Division of Organic Chemistry The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004