Hydroxyl-directed conjugate additions of carbon nucleophiles to cyclopentadienones

ORGN 890

Anthony J. Pearson and Ming Zhang, Ming.zhang1977@gmail.com. Department of Chemistry, Case Western Reserve University, 10900 Euclid Ave., Cleveland, OH 44106
The conjugate additions of different carbon nucleophiles to cyclopentadienone substrates (1 and 2) with one free hydroxyl functional group were investigated to determine the role of the hydroxyl group in determining regiochemistry. During this reaction an unexpected intramolecular displacement of OTBS by the enolate intermediate occurs, to afford cyclopropane derivatives.