[4 + 3] Cycloaddition of chiral allenamides

ORGN 192

Jennifer Antoline, antoline@chem.umn.edu, Richard P. Hsung, hsung@chem.umn.edu, and Jian Huang, huang@chem.umn.edu. Department of Chemistry, University of Minnesota-Twin Cities, 207 Pleasant St SE, Minneapolis, MN 55455
In recent years allenamides have emerged to become a synthetically useful functional group. The epoxidation of a chiral allenamide with DMDO provides access to a nitrogen stabilized oxyallyl cation. This reactive intermediate undergoes a diastereoselective [4 + 3] cycloaddition with a variety of dienes including pyrrole. The diastereoselectivity and regioselectivity of the reaction with a variety of substituted furans and pyrroles will be reported.

 

New Reactions and Methodology
8:00 AM-12:00 PM, Monday, 27 March 2006 Georgia World Congress Center -- C301, Oral

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006