Intramolecular anodic olefin coupling reactions: The use of N,O-ketene acetals as the initiating olefin reactions

ORGN 650

Yung tzung Huang and Kevin D. Moeller. Department of Chemistry, Washington University in St. Louis, Campus Box 1134, One Brookings Drive, St. Louis, MO 63130
Recent studies of intramolecular anodic olefin coupling reactions using ketene dithioacetals have shown that the subsequent radical cation intermediates are less reactive than radical cations derived from enol ethers. This observation suggests that the overall reactivity of an olefin coupling reaction may be tunable by adjusting the nature of the radical cation intermediate. For this reason, we have begun to study the utility of various ketene acetal based initiating groups for the cyclization reactions. Here we report that the use of an N,O-based ketene acetal leads to a radical cation that is more reactive than its enol ether counterpart. The results of these studies along with the potential of the reactions for developing asymmetric cyclizations will be presented.

 

New Reactions, Methodology, Heterocycles, Aromatics
8:00 PM-10:00 PM, Wednesday, August 25, 2004 Pennsylvania Convention Center -- Hall D, Poster

Division of Organic Chemistry

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