Halocycloalkenones are demonstrated to function as potent dienophiles in inter- and intramolecular Diels-Alder cycloadditions. 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 cyclopropyl functional handles is described.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3543988 | PMC |
| http://dx.doi.org/10.1021/jo302230m | DOI Listing |
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