Catalytic asymmetric [4 + 3] cycloadditions via epoxidation of allenamides

ORGN 14

Jian Huang and Richard P. Huang. Department of Chemistry, University of Minnesota, 207 Pleasant St. SE, Minneapolis, MN 55455
Synthetic utility of allenamides, electron-deficient variants of allenamines, has recently attracted much attention because of their enaminelike structure and stability. Although the stereoselective [4+3] cycloadditions using chiral allenamides have been reported, the catalytic asymmetric [4 + 3] cycloaddition of achiral allenamides remains unexlpored. We disclosed that epoxidation of allenamides using chiral catalyst could lead to enantioselective [4+3] cycloadditions. The determination of enantiomeric excess (% ee) in these reactions will also be reported.

 

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

Division of Organic Chemistry

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