Halocycloalkenones as Diels-Alder Dienophiles. Applications to Generating Useful Structural Patterns

Halocycloalkenones are demonstrated to function as potent dienophiles in inter- and intramolecular Diels Alder cydoadditions. We have found 2-brominated cycloalkenone dienophiles to be both highly endo selective and significantly more reactive than their nonhalogenated parent compounds. A method for the facile conversion of brominated cyclobutanone DA adducts to synthetically useful cydopropyl functional handles is described.