Rhodium catalyzed [4+2+2] cycloaddition and alkyne insertion: A new route to eight member rings

ORGN 34

W. Richard Counts1, Brenton DeBoef1, and Scott R. Gilbertson2. (1) Department of Chemistry, Washington University St Louis, One Brookings Drive, Campus Box 1134, St. Louis, MO 63130, (2) Chemical Biology Program, Department of Pharmacology & Toxicology, The University of Texas Medical Branch, 301 University Blvd., Galveston, TX 77555
A novel variation of the rhodium catalyzed 4+2 reaction is reported. A catalyst system that forms an eight-member ring product from the incorporation of an alkyne into a dienyne is discussed. The products are formed with high diastereoselectivity and in good yield. Examples of substitutions on the diene moiety of the dienyne are presented. Implications of this study toward future substrate design and reaction scope will be discussed.

 

Metal-Mediated Reactions and Syntheses
8:00 AM-12:00 PM, Sunday, August 22, 2004 Pennsylvania Convention Center -- 201B, Oral

Division of Organic Chemistry

The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004