Transition-metal catalyzed protocol for rapid assembly of polycyclic compounds

ORGN 443

Kay M. Brummond and Lingfeng You. Department of Chemistry, University of Pittsburgh, 234 Chevron Science Center, Pittsburgh, PA 15213
We discovered a concise way of making polycyclic compounds. The protocol involves a serialization of Alder-ene / intramolecular Diels-Alder / intermolecular Diels-Alder reactions in one pot. When allenediyne 1 is subjected to Rh(I) catalysis and dienophile 2, 3 is formed in 50-80% yield stereoselectively. The stereo- and regioselectivity, transition metal catalyst, scope and limitations of this protocol will be discussed.

 

Physical Organic, Materials, Heterocycles, Aromatics, Metal-Mediated Reactions
8:00 PM-10:00 PM, Tuesday, September 9, 2003 Hilton New York -- Americas Hall 1, Poster

Division of Organic Chemistry
The 226th ACS National Meeting, New York, NY, September 7-11, 2003